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

HRID 729595

Reaction equation

HRID 729595 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 for 1 hour at 100° C. Then add benzyl bromide (584.04 mmol, 69.46 mL) and stir overnight. Cool down 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. 1H NMR (CDCl3, 300 MHz): δ ppm :7.36-7.32 (m, 5H), 5.1 (s, 2H), 3.5 (s, 2H), 1.21 (s, 6H).

Workup

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

Sources & evidence

ORD record
ord-dbc2e2a6b2624307b2c09ace19340ad6
Source dataset
uspto-grants-2009_09
Patent number
US07582638B2

Linked notes

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