1-Butanol → Butyl Glycolate

HRID 2050770Notes

Reaction equation

HRID 2050770 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:17](O)(=[O:20])[CH2:18][OH:19].O>C1C=CC=CC=1>[C:18]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])(=[O:19])[CH2:17][OH:20]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 757Glycolic AcidHCID 962Water2×HCID 6101p-Toluenesulfonic acid

Product 1

HCID 81882Butyl Glycolate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To 101 g (1.5 moles) of butyl alcohol containing 5 g of ρ-toluene sulfonic acid in 325 ml of benzene at reflux was added dropwise 150 g (ca. 1.5 moles acid) of 70% glycolic acid. The flask was equipped with a Dean-Stark trap to collect the 30% of water from the aqueous glycolic acid mixture and to collect the 27 g (1.5 moles) of water liberated during the reaction--a total of ca. 68 ml. The benzene solution of the product was water washed and dried over anhydrous sodium sulfate. The benzene was stripped off on a rotary evaporator. A short pass distillation at reduced pressure produced a good grade butyl glycolate. The structure was established by infrared and nuclear magnetic resonance spectroscopy.

Workup

  1. customThe flask was equipped with a Dean-Stark trap
  2. customto collect the 30% of water from the aqueous glycolic acid mixture
  3. customliberated during the reaction
  4. washwashed
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe benzene was stripped off on a rotary evaporator
  7. distillationA short pass distillation at reduced pressure

Sources & evidence

ORD record
ord-2eeab0456a4242f58b7a0ef4dc84394f
Source dataset
uspto-grants-1991_05
Patent number
US05015419

Reaction notes

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