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公开(公告)号：DE3322995A1
公开(公告)日：1983-12-29
申请号：DE3322995
申请日：1983-06-25
Applicant: BASF AG
IPC: C07D311/72 , C07F3/02 , C07F9/143 , C07F9/54 , C07F9/40
Abstract: Compounds of the general formula I in which R denotes H, an alkyl radical, arylalkyl radical or an aliphatic acyl radical, preferably a benzyl group or acetyl group, and Y represents OH and X represents H (Ia) or else X and Y together represent a further bond between the C atoms carrying X and Y (Ib) and the dashed line may denote an additional bond, in particular [2R,1'Z,3'E,7'E]-6-benzyloxy-2,5,7,8-tetramethyl-2-(4',8',12'- trimethyltrideca-1',3',7'-trien-1'-yl)chroman and 6-benzyloxy-2,5,7,8- tetramethyl-2-(1'-hydroxy-4',8',12'-trimethyltrideca-3',7'-dien-1-yl)- chroman, and compounds of the general formula II in which Z represents one of the groups ClMg-; BrMg- (IIa); CL ; BR - (IIb> in which R represents alkyl having 1 to 4 C atoms, in particular (3,7,11-trimethyltrideca-2,6,10-trien-1-yl)triphenylphosphonium chloride and dimethyl (3,7,11-trimethyltrideca-2,6,10-trien-1-yl)- phosphite. The invention furthermore relates to a process for the preparation of (2R,4'RS,8'RS)- alpha -tocopherol or (all-rac)- alpha -tocopherol, starting from the compounds of the formula II and via the compounds of the formula I.
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公开(公告)号：DE3145486A1
公开(公告)日：1983-05-19
申请号：DE3145486
申请日：1981-11-16
Applicant: BASF AG
IPC: C07C17/00 , C07C17/16 , C07C17/26 , C07C17/354 , C07C19/01 , C07C19/075 , C07C31/36 , C07C45/40 , C07C47/14 , C07C51/16 , C07C51/56 , C07C55/02 , C07D315/00 , C07C69/63 , C07C19/02 , C07C67/00
Abstract: Novel optically active alkyl 5-chloro- and 5-bromo-3-methylpentanoates of the general formula I in which Y represents Cl or Br and R represents a lower alkyl radical, a process for their preparation which is characterised in that an optically active 3-methylpentane-1,5-dioic acid monoalkyl ester of the general formula II in which R has the abovementioned meaning, is converted into an optically active 3-methylvalerolactone by selective reduction of the acid group or by selective reduction of the ester group and this lactone is treated at 0 to 50 DEG C with a solution of hydrogen chloride or hydrogen bromide in an alkanol ROH, and their use as optically active intermediates for the preparation of the C15-building blocks required for the synthesis of the side chain of (R,R,R)- alpha -tocopherol, and a process for the preparation of (3R,7R)-1-chloro- and (3R,7R)-1-bromo-3,7,11-trimethyldodecane starting from (R)-5-chloro- and (R)-5-bromo-3-methylpentanoic esters.
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公开(公告)号：DE3030054A1
公开(公告)日：1982-03-25
申请号：DE3030054
申请日：1980-08-08
Applicant: BASF AG
IPC: C07C67/00 , C07C215/10 , C07C241/00 , C07C245/08 , C07D475/00 , C07D475/14 , C09B29/085 , C07C107/06
Abstract: A process for the preparation of N-(D)-ribityl-2-phenylazo-4,5-dimethylaniline (I), wherein 1. in the case of pure or virtually pure (D)-ribose (III) (a) the latter is reacted with 3,4-dimethylnitrobenzene (IVa) or 3,4-dimethylaniline (IVb) and with hydrogen in the presence of a hydrogenation catalyst, (b) the resulting solution is reacted, in a conventional manner, with an acid phenyldiazonium salt solution (VI) and (c) the resulting product is isolated by crystallization, in a conventional manner, or 2. in the case of crude ribose, ie. industrial mixtures of (D)-ribose and other sugars (a) the crude ribose is reacted with about equimolar amounts, based on III, of 3,4-dimethylaniline (IVb) and boric acid, (b) the boric acid ester of the Schiff base obtained from III and IVb is allowed to crystallize out and is separated off, (c) this ester is hydrogenated with hydrogen in the presence of a hydrogenation catalyst, (d) the solution is freed from catalyst and reacted, in a conventional manner, with an acid phenyldiazonium salt solution and (e) the resulting product I is isolated by crystallization in a conventional manner.
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公开(公告)号：DE2947797A1
公开(公告)日：1981-07-30
申请号：DE2947797
申请日：1979-11-28
Applicant: BASF AG
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公开(公告)号：DE2842715A1
公开(公告)日：1980-04-10
申请号：DE2842715
申请日：1978-09-30
Applicant: BASF AG
IPC: C07D319/06
Abstract: 3-Chloro-3-methyl-butane-1,4-dial-bis-acetals and 3-methyl-but-2-ene-1,4-dial-bis-acetals are obtained by reacting a six-membered cyclic acetal of 3-methyl-but-3-en-1-al with an alkyl nitrite in the presence of methanol and hydrogen chloride and, if desired, eliminating HCl in the conventional manner. The butanedial-bis-acetals and butenedial-bis-acetals are valuable intermediates through which the trans-3-methyl-but-2-ene-1,4-dial-1-acetals, which are sought-after products for terpene syntheses, can be obtained in an industrially particularly advantageous manner.
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Patent Agency Ranking
公开(公告)号：DE2842238A1
公开(公告)日：1980-04-10
申请号：DE2842238
申请日：1978-09-28
Applicant: BASF AG
Inventor： FISCHER ROLF DIPL CHEM DR , WEITZ HANS-MARTIN DIPL CHEM DR , PAUST JOACHIM DIPL CHEM DR , JAEDICKE HAGEN DIPL CHEM DR
IPC: C07C47/277 , C07C67/05 , C07C69/007 , C07C69/18
Abstract: Triacyloxybutene derivs. of formula (I) R2-COO-C(OCOR3) H-CH=CR1-CH2.OCOR3 are new. In (I), R1 is 1-5C alkyl; and R2 and R3 are each H, 1-5C alkyl, phenyl or cyclohexyl. Pref. cpds. have R1=R2=CH3; R3 = CH3 or C2H5 (I). are made by reacting a 1-acyloxy-3-R1-1,3-butadiene with R3COOH in presence of O2 and Pt or Pd catalyst. (I) are intermediates for terpenes and pharmaceuticals esp. they can be hydrolysed to 4-acyloxy-3-methylcrotonaldehydes (IX) which are C5-units for terpene synthesis. 1,4,4-Triacetoxy-3-methyl-2-butene is specifically claimed.
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公开(公告)号：DE3210706A1
公开(公告)日：1983-10-06
申请号：DE3210706
申请日：1982-03-24
Applicant: BASF AG
Abstract: 2-alkyl-4,4-diacyloxybut-2-enals of the formula I where R1 is alkyl and R2 and R3 are each hydrogen or an aliphatic, cycloaliphatic or aromatic radical, are prepared by a process wherein a 2-alkyl-2,4-diacyloxybut-3-enal of the formula II is treated with an aliphatic carboxylic acid.
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公开(公告)号：DE3145454A1
公开(公告)日：1983-05-26
申请号：DE3145454
申请日：1981-11-16
Applicant: BASF AG
IPC: C07C17/093 , C07C17/26 , C07C19/01 , C07C19/075 , C07C53/19 , C07D315/00 , C07C19/02 , C07C59/19
Abstract: 1-Bromo-4-chloro-2-methylbutane, (S)-1-bromo-4-chloro- 2-methylbutane (V) and (R)-5-chloro-3-methylpentanoic acid (Va) and the use of (S)-3-methylvalerolactone, (S)-1-bromo-4-chloro- 2-methylbutane (V) or (R)-5-chloro-3-methylpentanoic acid (Va) as optically active intermediates for the synthesis of the side chain of (R,R,R)- alpha -tocopherol and a process for the preparation of (3R,7R)-1-chloro-3,7,11-trimethyldodecane of the formula Ia in which n is 1, characterised in that A) (S)-3-methylvalerolactone of the formula IV is cleaved using liquid hydrogen chloride at 100 to 170 DEG C in a pressurised vessel to give the novel (3R)-5-chloro-3-methylpentanoic acid of the formula Va B) this acid is converted in a manner known per se into the novel dihalide of the formula IIa in which X represents Br or I, by decarboxylation with bromine or iodine, and C) this dihalide is reacted in the presence of copper ions with an organomagnesium compound of the formula IIIa in which Y represents Cl, Br or I and n represents 1, at temperatures below 0 DEG C in an ether solvent, preferably tetrahydrofuran.
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公开(公告)号：DE3145436A1
公开(公告)日：1983-05-26
申请号：DE3145436
申请日：1981-11-16
Applicant: BASF AG
Inventor： VOGEL FRIEDRICH DIPL CHEM , PAUST JOACHIM DIPL CHEM DR
IPC: C07C17/093 , C07C17/16 , C07C17/26 , C07C19/075 , C07C29/147 , C07C31/36 , C07C309/73 , C07C19/02 , C07C143/68
Abstract: Novel optically active compounds of the general formula I in which Y represents chlorine or bromine and Z represents OH, Cl, Br, I or -OSO2R, in which R denotes -CH3; -C2H5-; -C3H8 or -C4H9, in particular (R)-5-chloro-3-methylpentanol, (R)-5-bromo-3-methylpentanol, (S)-1-bromo-5-chloro-3-methylpentane, (R)-1-bromo-5-chloro-3-methylpentane, their use for the preparation of optically active compounds of the general formula II in which Y represents Cl or Br, and a process for the preparation of the compounds of the formula I, which is characterised in that the corresponding novel optically active alkyl 5-halo-3-methylpentanoates of the general formula III in which R represents alkyl having 1 to 4 C atoms, are reduced with lithium aluminium hydride or lithium borohydride to the optically active 5-halo-3-methylpentanol of the formula Ia and this pentanol is reacted in the presence of bases with p-toluenesulphonyl chloride or halogenated in a manner known per se.
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公开(公告)号：DE3145485A1
公开(公告)日：1983-05-19
申请号：DE3145485
申请日：1981-11-16
Applicant: BASF AG
IPC: C07C29/32 , C07C33/025 , C07C45/40 , C07D309/10
Abstract: (R)-3,7-Dimethyl-5-octen-1-ol of the formula I its use as optically active intermediate for the synthesis of the side chain of (R,R,R)- alpha -tocopherol and a process for its preparation which is characterised in that A) (3S)-3-methylvalerolactone of the formula II is reduced in a manner known per se to (4S)-2-hydroxy-4-methyltetrahydropyran of the formula III and B) this tetrahydropyran is reacted with a phosphorus ylide of the general formula IV in which Ar represents identical or different aryl radicals or cyclohexyl radicals, preferably phenyl or tolyl, in a Wittig reaction.
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