Hydroquinone → n-Butyl farnesylacetate

HRID 436885Notes

Reaction equation

HRID 436885 reaction equation
[C:1]([O-:9])([O-])([O:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH3:2].O[C:11]([CH2:15][CH2:16][CH:17]=[C:18]([CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH3:19])([CH:13]=[CH2:14])[CH3:12].C1(C=CC(O)=CC=1)O>C(O)CCC>[CH2:14]([CH2:2][C:1]([O:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:9])[CH:13]=[C:11]([CH2:15][CH2:16][CH:17]=[C:18]([CH2:20][CH2:21][CH:22]=[C:23]([CH3:24])[CH3:25])[CH3:19])[CH3:12]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 88883,7,11-Trimethyldodeca-1,6,10-trien-3-olHCID 86734837n-Butyl orthoacetate

Product 1

HCID 54335387n-Butyl farnesylacetate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Following the same procedures as in Example 26, a mixture of 1184 g. of n-butyl orthoacetate, 220 g. of nerolidol and 22 g. of hydroquinone was reacted with heating at 160° - 165° C., with removal of n-butanol produced from the reaction system. The reaction mixture was directly distilled in vacuo to give 598 g of n-butyl farnesylacetate, b.p. 134° - 142° C. (0.3 mmHg). Then, this product was fractionated through a rectifying column with 40 numbers of theoretical plates reflux ratio of 20 to give 147.5 g of n-butylΔ 4,8 -trans-farnesylacetate, b.p. 140° - 142° C. (0.3 mmHg). 64% of Δ4,8 -trans-isomer introduced was recovered on distillation.

Workup

  1. additiona mixture of 1184 g
  2. customproduced from the reaction system
  3. distillationThe reaction mixture was directly distilled in vacuo

Sources & evidence

ORD record
ord-6648c46136c249d88444574c89417980
Source dataset
uspto-grants-1977_06
Patent number
US04028385

Reaction notes

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