Phosphoric Acid → Isobutyl 3,4-epoxybutyrate

HRID 2291678Notes

Reaction equation

HRID 2291678 reaction equation
P(=O)(O)(O)O.S(=O)(=O)(O)[OH:7].[C:11]([O:16][CH2:17][CH:18]([CH3:20])[CH3:19])(=[O:15])[CH2:12][CH:13]=[CH2:14]>O.ClCCCl.O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:19][CH:18]([CH3:20])[CH2:17][O:16][C:11](=[O:15])[CH2:12][CH:13]1[O:7][CH2:14]1

Participants

7

Reactant 3

HCID 1004Phosphoric AcidHCID 1118Sulfuric AcidHCID 528715Isobutyl but-3-enoate

Product 1

HCID 5463767Isobutyl 3,4-epoxybutyrate

Reagents, catalysts & solvents 3

HCID 150191Sodium Tungstate DihydrateCatalystHCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Sodium tungstate dihydrate (0.852 g, 2.5 mmol), 85% phosphoric acid (0.850 ml, 5 mmol) 36.3% hydrogen peroxide (5.6 ml, 60 mmol) were dissolved in 20 ml of water and the pH was adjusted to 1.6 by 10% sulphuric acid. The solution was heated to 70° C., and under vigorous stirring a solution of 2-methylpropyl 3-butenoate (7.1 g, 50 mmol), trimethylcaprylammonium chloride (0.41 g) in 1,2-dichloroethane (15 ml) was added. After 6 hours the mixture was cooled, then the layers were separated. The aqueous phase was washed with 30 ml of dichloroethane. Organic layers were collected, washed with 2×40 ml of saturated solution or sodium sulphite, dried and distilled. The title compound was obtained as a colourless oil, b.p. 104°-108° 30 mmHg.

Workup

  1. additionwas added
  2. temperatureAfter 6 hours the mixture was cooled
  3. customthe layers were separated
  4. washThe aqueous phase was washed with 30 ml of dichloroethane
  5. customOrganic layers were collected
  6. washwashed with 2×40 ml of saturated solution or sodium sulphite
  7. customdried
  8. distillationdistilled

Sources & evidence

ORD record
ord-0a4fb0d78c444a2a9084fa4fb7efce15
Source dataset
uspto-grants-1989_01
Patent number
US04797496

Reaction notes

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