Potassium Hydroxide → 3-(Benzyloxy)-2,2-dimethylpropanoic acid

HRID 1802415Notes

Reaction equation

HRID 1802415 reaction equation
[OH-].[K+].C[O:4][C:5](=[O:18])[C:6]([CH3:17])([CH3:16])[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[CH2:9]([O:8][CH2:7][C:6]([CH3:17])([CH3:16])[C:5]([OH:18])=[O:4])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59267989Methyl 3-(benzyloxy)-2,2-dimethylpropanoate

Product 1

HCID 134782883-(Benzyloxy)-2,2-dimethylpropanoic acidYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of potassium hydroxide (1.8 g, 338 mmol) and 3-benzyloxy-2,2-dimethyl-propionic acid methyl ester in ethanol (50.0 mL) is refluxed for 24 h. The solvent is removed under reduced pressure, the crude is diluted with water and extracted with ethyl acetate. The water phase is acidified with 1N aq. HCl (pH ˜2-3) and extracted with ethyl acetate. The combined organic layers are washed with water and brine; the organic phase is dried over Na2SO4, filtered and concentrated under reduced pressure to afford 2.5 g of 3-benzyloxy-2,2-dimethyl-propionic acid as a brown solid that is used in the next step without any further purification. Yield: 32%, over two steps; m/z 209 [M+H].

Workup

  1. customThe solvent is removed under reduced pressure
  2. additionthe crude is diluted with water
  3. extractionextracted with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers are washed with water and brine
  6. dry with materialthe organic phase is dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a410557ff2a24ad7912b4371e39491a0
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

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