Sulfuric Acid → Butyl tert-butoxyacetate

HRID 4370

Reaction equation

HRID 4370 reaction equation
[CH3:1][C:2](=[CH2:4])[CH3:3].[C:5]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])(=[O:8])[CH2:6][OH:7].S(=O)(=O)(O)O>C(Cl)Cl>[C:2]([O:7][CH2:6][C:5]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:8])([CH3:3])([CH3:1])[CH3:4]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 81882Butyl Glycolate

Product 1

HCID 14050415Butyl tert-butoxyacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 500-ml, thick-walled Erlenynmeyer flask equipped with a magnetic stirring bar was cooled to -78° C. (dry iece-acetone bath) and charged with isobutylene (150 ml). Then, n-butyl glycolate (20.0 g, 0.151 mol) and 50 ml of methylene chloride was added along with 1 ml of concentrated sulfuric acid. The cold bath was removed and the mixture stirred for 3 days at room temperature. The reaction was quenched with 50 ml of saturated sodium bicarbonate and the product extracted with ether. The ether layer was dried over sodium sulfate and concentrated. After distillation, the title compound was obtained as a colorless oil: bp 64°-65° C. (0.7 mm).

Workup

  1. customA 500-ml, thick-walled Erlenynmeyer flask equipped with a magnetic stirring bar
  2. customThe cold bath was removed
  3. customThe reaction was quenched with 50 ml of saturated sodium bicarbonate
  4. extractionthe product extracted with ether
  5. dry with materialThe ether layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. distillationAfter distillation

Sources & evidence

ORD record
ord-97da413a676c4eefa7c6d0c7176edaf1
Source dataset
uspto-grants-1988_02
Patent number
US04725620

Linked notes

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