Process
AssigneeGivaudan SA
InventorsFridtjof SCHROEDER, Martin LOVCHIK
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Abstract
Described herein are methods for making intermediates useful in the production of fragrance ingredients starting from myrcene. In particular, methods for making geranyl chloride, (E)-6,10-dimethylundeca-1,5,9-triene and (E)-6,10-dimethylundeca-5,9-dien-1-yne are described. Methods for making other intermediates in the process are also described.
Claims14
A method producing a purified form of geranyl chloride, a compound of Formula (I),
- wherein the method comprises:
- (i) a halogenation step comprising chlorinating a compound of Formula (II)
- with
- a) a chloroformate to produce a first reaction mixture comprising a compound of Formula (I) and a carbamate, or
- b) an acid chloride to produce a first reaction mixture comprising a compound of Formula (I) and an amide,
- and
- (ii) a distillation step, the distillation step comprising distilling a mixture comprising the first reaction mixture to produce a separated portion of the distillation mixture comprising a purified form of the compound of Formula (I) as compared to the first reaction mixture;
- and
- wherein Q is a a monovalent residue selected from N(methyl)2, N(ethyl)2, N(n-propyl)2, N(isopropyl)2, N(benzyl)2, N(CH3)CH2CH2NR2(CH3), N-methyl-N-ethyl-amine,
- and wherein
- n is selected from 1, 3 and 4;
- and
- A is selected from O and NR2 wherein R2 is selected from H and geranyl
The method of any preceding claim wherein the separated portion has a higher molar or weight ratio of the compound of Formula (I) to carbamate than the molar or weight ratio, respectively, of the compound of Formula (I) to carbamate in the first reaction mixture.
A method of producing a compound of Formula (IV),
- wherein the method comprises:
- (i) a halogenation step comprising chlorination of a compound of Formula (II) with
- a) a chloroformate to produce a first reaction mixture comprising a compound of Formula (I) and a carbamate, or
- b) an acid chloride to produce a first reaction mixture comprising a compound of Formula (I) and an amide
- wherein Q is a a monovalent residue selected from N(methyl)2, N(ethyl)2, N(n-propyl)2, N(isopropyl)2, N(benzyl)2, N(CH3)CH2CH2NR2(CH3), N-methyl-N-ethyl-amine,
- and wherein
- n is selected from 1, 3 and 4;
- and
- A is selected from O and NR2 wherein R2 is selected from H and geranyl;
- and
- (ii) a distillation step, the distillation step comprising distilling a mixture comprising the first reaction mixture to produce a separated portion of the distillation mixture comprising a purified form of the compound of Formula (I) as compared to the first reaction mixture;
- and
- (iii) contacting the separated portion with a nucleophile to produce a compound of formula (IV) wherein R1 is selected from furyl, phenyl, C1-C10 alkyl, C2-C10 alkyl comprising at least one double bond or triplet bond, C1-C10 alkyl-OH, C2-C10alkyl-OH comprising at least one double bond or one triplet bond, and —CH2-C≡C-Si-(R3)3 wherein each R3 is selected independently from C1-C5 alkyl.
Dependencies are inferred from the claim text.