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US 4,055,575 AGranted
Synthesis of dehydrophytol and vitamin E
AssigneeSCM Corporation
InventorsRalph E. Close, William Oroshnik
Life of this patent
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Abstract
A process for the synthesis of dehydrophytol and Vitamin E comprising forming a C.sub.15 acetylene from hexahydropseudoionone and then coupling said acetylene with 1-acetoxy-4-chloro-3-methylbut-2-ene to form a C.sub.20 acetoxy-enyne. The latter is readily subjected to partial hydrogenation and saponification in that order to form a dehydrophytol, a useful intermediate for the synthesis of Vitamin E and other products.
Claims7
A process for the synthesis of dehydro-Vitamin E comprising the steps of
- a. reacting hexahydropseudo-ionone with a metal acetylide to form 3,7,11-trimethyl-3-hydroxy-1-dodecyne;
- b. reacting the product of step a) with a reagent capable of replacing the hydroxyl group with a halogen to produce 3,7,11-trimethyl-3-halo-1-dodecyne;
- c. reducing the product of step b) to form the corresponding allene, said allene being 3,7,11-trimethyldodeca-1,2-diene;
- d. isomerizing the allene of step c) to 3,7,11-trimethyldodeca-1-yne in the presence of a strong base;
- e. coupling the acetylene of paragraph d) with a reactant having the general formula ##STR8## wherein R.sub.3 is a halogen and R.sub.1 is an hydroxyl or carboxylic acid ester group;
- f. hydrogenating and saponifying the coupling product to dehydrophytol;
- and
- g. coupling the product of step (f) with trimethylhydroquinone.
5 more elements
Dependencies are inferred from the claim text.