a Farnesol → Isophytol

HRID 2188330Notes

Reaction equation

HRID 2188330 reaction equation
O[CH2:2][CH:3]=C(CCC=C(CCC=C(C)C)C)C.CC(C)=CCC/C(/C)=C/CC/C(/C)=C/C=O.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].[CH3:46][CH:47]([CH2:54][CH2:55][CH2:56][CH:57]([CH3:64])[CH2:58][CH2:59][CH2:60][CH:61]([CH3:63])[CH3:62])[CH2:48][CH2:49][CH2:50][C:51](=[O:53])[CH3:52].[C-]#[C-]>CC(C)=O>[CH3:62][CH:61]([CH2:60][CH2:59][CH2:58][CH:57]([CH2:56][CH2:55][CH2:54][CH:47]([CH2:48][CH2:49][CH2:50][C:51]([OH:53])([CH:2]=[CH2:3])[CH3:52])[CH3:46])[CH3:64])[CH3:63]

Participants

7

Reactant 5

HCID 3327a Farnesol2×HCID 104082-pentadecanone, 6,10,14-trimethyl-2×HCID 11143Aluminum isopropoxideHCID 5280598(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal2×HCID 178420940HCID 178420940, compound

Product 1

HCID 10453Isophytol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A particularly preferred embodiment of synthesizing vitamin E from farnesol is illustrated in FIG. 3. Farnesol 3-8 is oxidized to farnesal 3-9 under Oppenauer oxidation conditionS using aluminum isopropoxide and acetone. Farnesal 3-9 is then converted to dehydrofarnesyl acetone 3-10 by an aldol condensation reaction with acetone. Reduction of olefin moieties on dehydrofarnesyl acetone 3-10 by hydrogenation then produces 6,10,14-trimethyl pentadecan-2-one 3-11. Addition of acetylide to the ketone 3-11 then generates propargylic alcohol 3-12 which is partially reduced using Lindlar hydrogenation condition to produce isophytol 3-13. Reaction of isophytol 3-13 with 2,3,5-trimethyl hydroquinone 3-5 in the presence of an acid catalyst then produces vitamin E.

Sources & evidence

ORD record
ord-c7cd6082633c42a9b7eb0ec198a7acf2
Source dataset
uspto-grants-2002_06
Patent number
US06410755B1

Reaction notes

Loading…