Methanol → 3-(Benzyloxy)-2,2-dimethylpropanoic acid
Reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH3:14])([CH3:13])[C:11]#N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:15].[Na+].C[OH:18]>>[CH2:1]([O:8][CH2:9][C:10]([CH3:14])([CH3:13])[C:11]([OH:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
A mixture of 3-benzyloxy-2,2-dimethylpropanenitrile (2.5 g, 13.2 mmol), 10% aqueous sodium hydroxide (10 mL) and methanol (150 mL) was heated 8 hours at reflux and then concentrated. The residue was dissolved in water (30 mL) and the solution was washed with dichloromethane (2×10 mL), treated with 10% hydrochloric acid and extracted with ethyl acetate (4×20 mL). The combined extracts were washed with water and brine, dried (MgSO4) and concentrated to give 3-benzyloxy-2,2-dimethylpropionic acid (1.6 g, 7.5 mmol).
Workup
- temperaturewas heated 8 hours
- temperatureat reflux
- concentrationconcentrated
- dissolutionThe residue was dissolved in water (30 mL)
- washthe solution was washed with dichloromethane (2×10 mL)
- additiontreated with 10% hydrochloric acid
- extractionextracted with ethyl acetate (4×20 mL)
- washThe combined extracts were washed with water and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8fa29025fb3f4853910878d3a66ac35e
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05859014
Reaction notes
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