Benzene → 9-Tetradecen-1-ol, 1-formate, (9Z)-

HRID 2083080Notes

Reaction equation

HRID 2083080 reaction equation
[CH:1]([OH:3])=[O:2].O.CCO[CH2:8][CH3:9].[CH:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH:1]([O:3][CH2:14][CH2:15][CH2:10][CH2:11][CH2:12][CH2:13][CH2:10][CH2:15]/[CH:14]=[CH:13]\[CH2:12][CH2:11][CH2:8][CH3:9])=[O:2]

Participants

5

Reactant 4

HCID 241BenzeneHCID 284Formic AcidHCID 962WaterHCID 3283Diethyl Ether

Product 1

HCID 53675999-Tetradecen-1-ol, 1-formate, (9Z)-Yield 78%

Procedure

A mixture of 11 g of compound VI and 11 g of 97% formic acid in 50 ml of dry benzene was relfuxed for 6 hours, continuously removing the water formed with a Dean-Stark trap. The cooled solution was treated with 100 ml each of H2O and ether, and the organic layer was washed several times with cold H2O, 10% NaHCO3 solution, and saturated with NaCl solution, then dried with Na2SO4. Evaporation of solvent and distillation gave 9.7 g (78%) of compound I as a colorless liquid boiling at 103°-108° (0.2 mm), ND25 1.4464.

Workup

  1. customcontinuously removing the water
  2. customformed with a Dean-Stark trap
  3. washthe organic layer was washed several times with cold H2O, 10% NaHCO3 solution
  4. dry with materialsaturated with NaCl solution, then dried with Na2SO4
  5. customEvaporation of solvent and distillation

Sources & evidence

ORD record
ord-58098d9b557c4654b7a25077065316dc
Source dataset
uspto-grants-1978_04
Patent number
US04083995

Reaction notes

Loading…