Acetic Acid → 59694-62-1

HRID 1446890Notes

Reaction equation

HRID 1446890 reaction equation
[CH2:1]([OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[C:13](O)(=[O:15])[CH3:14].O.OS(O)(=O)=O>>[C:13]([O:12][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])(=[O:15])[CH3:14]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 371531,10-Decanediol

Product 1

HCID 1100936559694-62-1Yield 79%

Procedure

A solution of 4.36 g (25 mmoles) of 1,10-decanediol in 100 ml (1.77 moles) of glacial acetic acid was mixed with 130 ml (7.22 moles) of H2O containing 0.25 ml (4.5 mmoles) of conc. H2SO4. This mixture, itself at room temperature, was then extracted continuously for two days using refluxing cyclohexane. The cyclohexane layer was then cooled to room temperature and 0.78 g (18% recovery) of crystalline 1,10-decanediol was recovered by simple filtration of this nonpolar organic phase. The cyclohexane was then removed from the filtrate under reduced pressure, affording 4.28 g (approximately 79% yield--97% based on recovered starting material of product. GC analysis showed the presence of less than 2% starting diol; the ratio of monoester to diester was 20 to 1. Hence the desired monoester was approximately 95% pure.

Workup

  1. extractionThis mixture, itself at room temperature, was then extracted continuously for two days
  2. temperatureusing refluxing cyclohexane
  3. filtration0.78 g (18% recovery) of crystalline 1,10-decanediol was recovered by simple filtration of this nonpolar organic phase
  4. customThe cyclohexane was then removed from the filtrate under reduced pressure
  5. customaffording 4.28 g (approximately 79% yield--97%
  6. customon recovered

Sources & evidence

ORD record
ord-3061c3910b1e4b1685298e2159d8878d
Source dataset
uspto-grants-1982_02
Patent number
US04314071

Reaction notes

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