Acetic Acid → (4-Octylphenyl)methanol

HRID 65270Notes

Reaction equation

HRID 65270 reaction equation
[CH2:1]([C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([O-])(=[O:19])C.[K+].C(O)(=O)C>O>[CH2:1]([C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:19])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517044Potassium AcetateHCID 122531771-(Chloromethyl)-4-octylbenzene

Product 1

HCID 14763613(4-Octylphenyl)methanolYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 16.2 g (68 mMols) of 4-octylbenzyl chloride, 41,8 g (0.43 mols) of potassium acetate and 200 ml of glacial acetic acid was heated for 20 h to 130° C. After cooling, the mixture was poured into approximately 1 liter of water and the aqueous phase was extracted with tert.-butyl methyl ether. The organic phase was washed twice with water, repeatedly with potassium hydrogen carbonate solution (2N) and then with saturated sodium chloride solution. After the solvent had been distilled off, the residue was taken up in 160 ml of 1,2-dimethoxyethane and, after the addition of 64 g of sodium hydroxide in 130 ml of water, the solution was heated for 45 h to boiling point. After the solvent had been distilled off, the residue was extracted with tert.-butyl methyl ether, the ether phase was washed with water, the solvent was distilled off, the residue was taken up in petroleum ether and the solution was reconcentrated by evaporation after treatment with active carbon and fuller's earth. Fractionation under reduced pressure produced 8 g (54% of theoretical) of 4-octylbenzyl alcohol boiling at 128° C./0.11 mbar and having a refractive index n of 1.5033.

Workup

  1. temperaturewas heated for 20 h to 130° C
  2. temperatureAfter cooling
  3. extractionthe aqueous phase was extracted with tert.-butyl methyl ether
  4. washThe organic phase was washed twice with water, repeatedly with potassium hydrogen carbonate solution (2N)
  5. distillationAfter the solvent had been distilled off
  6. additionafter the addition of 64 g of sodium hydroxide in 130 ml of water
  7. temperaturethe solution was heated for 45 h
  8. distillationAfter the solvent had been distilled off
  9. extractionthe residue was extracted with tert.-butyl methyl ether
  10. washthe ether phase was washed with water
  11. distillationthe solvent was distilled off
  12. customthe solution was reconcentrated by evaporation after treatment with active carbon and fuller's earth

Sources & evidence

ORD record
ord-33590d13efa24bb1853481e668b22728
Source dataset
uspto-grants-1986_09
Patent number
US04613622

Reaction notes

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