Reaction #1534072

Reaction equation

1,10-decanediol

acetic acid

H2O

H2SO4

→

1,10-decanediol monoacetate

Yield 79.0%

Conditions

Workup

1. 1
   ExtractionThis mixture, itself at room temperature, was then extracted continuously for two days
2. 2
   Temperatureusing refluxing cyclohexane
3. 3
   Filtration0.78 g (18% recovery) of crystalline 1,10-decanediol was recovered by simple filtration of this nonpolar organic phase
4. 4
   OtherThe cyclohexane was then removed from the filtrate under reduced pressure
5. 5
   Otheraffording 4.28 g (approximately 79% yield--97%
6. 6
   Otheron recovered

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.

Source