Water → Benzyl 3-hydroxy-2,2-dimethylpropanoate

HRID 1993672

Reaction equation

HRID 1993672 reaction equation
[OH-].[K+].O[C:4]([CH3:10])([CH2:8][OH:9])[C:5]([OH:7])=[O:6].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O.[CH3:20]N(C=O)C>C(OCC)(=O)C>[CH2:11]([O:7][C:5](=[O:6])[C:4]([CH3:10])([CH3:20])[CH2:8][OH:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 5607812-Methylglyceric acid

Product 1

HCID 18922595Benzyl 3-hydroxy-2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
100 °C

Procedure

Add potassium hydroxide (486.7 mmol, 32.1 g) over a solution of 2,3-dihydroxy-2-methyl-propionic acid (423.2 mmol, 50 g) in 300 mL of DMF. Stir the solution for 1 hour at 100° C., then add benzyl bromide. Stir the solution overnight. Cool the mixture and dilute with ethyl acetate. Wash organic layer with water. Wash aqueous layer with ethyl acetate several times. Combine organic layers and dry over sodium sulfate, filter and concentrate under reduced pressure.

Workup

  1. stirringStir the solution overnight
  2. temperatureCool the mixture
  3. dry with materialCombine organic layers and dry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-47c92e3d87394898bcbcff1ac92ca457
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Linked notes

Loading…