Acetic Acid → 8-Hydroxyoctyl acetate

HRID 1446891Notes

Reaction equation

HRID 1446891 reaction equation
[CH2:1]([OH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].[C:11](O)(=[O:13])[CH3:12].O.OS(O)(=O)=O>>[C:11]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:10])(=[O:13])[CH3:12]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 694201,8-Octanediol

Product 1

HCID 2511478-Hydroxyoctyl acetateYield 92.3%

Procedure

A solution of 1.987 g (13.7 mmoles) of 1,8-octanediol in 25 ml (441 mmoles) of glacial acetic acid was mixed with 200 ml (11.11 moles) of H2O containing 4 ml (72 mmoles) of conc. H2SO4. This mixture was extracted continuously for 40 hours using hexane. The monoester is not very soluble in hexane and hence a mixture of hexane-cyclohexane (in which the monoester, but not the starting diol, is soluble) should be recommended if one is interested in developing this process for 1,8-octanediol. After cooling the hexane to room temperature, ether was added to make the organic layer homogeneous. The ether-hexane layer was then dried over anhydrous potassium carbonate and filtered. Removal of the solvent under reduced pressure afforded 2.38 g (~92% yield) of product, GC analysis of which indicated the presence of 2% starting diol and 4% diester. The purity of the desired monoester was therefore 94%.

Workup

  1. extractionThis mixture was extracted continuously for 40 hours
  2. additionhence a mixture of hexane-cyclohexane (in which the monoester
  3. additionether was added
  4. dry with materialThe ether-hexane layer was then dried over anhydrous potassium carbonate
  5. filtrationfiltered
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-6d4770ad865e44758ced889d6883b0fe
Source dataset
uspto-grants-1982_02
Patent number
US04314071

Reaction notes

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