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

HRID 1442381Notes

Reaction equation

HRID 1442381 reaction equation
[OH:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C)C=O>[OH:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4]([O:6][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 785483-Hydroxy-2,2-dimethylpropionic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of hydroxypivalic acid (3 g) and potassium carbonate (3.9 g) in N,N-dimethylformamide (25 mL) was added benzyl bromide (2.9 mL), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water twice and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (4.7 g).

Workup

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe organic layer was washed with water twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ceb223e907604f25817a8f1fbcded460
Source dataset
uspto-grants-2010_02
Patent number
US07655632B2

Reaction notes

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