Ethanol → 3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol

HRID 1377119Notes

Reaction equation

C(O)C.[OH-].[Na+].[N+](C1C=CC(C([O:15][CH2:16]/[CH:17]=[C:18](/[CH2:20][CH2:21]/[CH:22]=[C:23](\[CH3:35])/[CH2:24][CH2:25]/[CH:26]=[C:27](/[CH2:29][CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])\[CH3:28])\[CH3:19])=O)=CC=1)([O-])=O>O.C1(C)C=CC=CC=1>[CH2:25]([CH2:24][C:23](=[CH:22][CH2:21][CH2:20]/[C:18](=[CH:17]/[CH2:16][OH:15])/[CH3:19])[CH3:35])/[CH:26]=[C:27](/[CH2:29][CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])\[CH3:28]

Participants

Conditions

Temperature: 50 °C

Procedure

100 g of ethanol, 7.88 g of sodium hydroxide and 30 g of water were added to 75 g of geranylgeranyl p-nitrobenzoate (containing 0.98 g of geranylneryl p-nitrobenzoate and 67.35 g of geranylgeranyl p-nitrobenzoate) obtained as a cake in Example 7. The reaction mixture was stirred at 50°C. for 2 hours and cooled down to room temperature, to which 300 g of toluene and 200 g of water were added. The resulting organic phase was separated and washed twice with 200 g of water, and concentrated under reduced pressure to give 55 g of crude geranylgeraniol. This crude product was subjected to simple distillation (154°C., 0.5 mmHg) to give 42.1 g of a main fraction. The results of the analysis of the obtained fraction with gas chromatography under the same conditions as in Example 14 revealed that it contained geranylgeraniol with a purity of 97.8% and geranylnerol with a purity of 1.2%.

Workup

customobtained as a cake in Example 7
additionwere added
customThe resulting organic phase was separated
washwashed twice with 200 g of water
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d399c31cfda84e54a48c91e9eddec8a1
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05663461

Reaction notes

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