Toluene → Ethyl 4-isobutylbenzoate
Reaction equation
C([C:3]([CH2:10][CH3:11])([CH2:8][CH3:9])[C:4]([O-:7])([O-:6])[O-])C.[CH2:12]([C:16]1C=CC=CC=1C(O)=O)[CH:13]([CH3:15])[CH3:14].[C:25]1(C)C=CC=C[CH:26]=1>>[CH2:12]([C:16]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH2:25][CH3:26])=[O:7])=[CH:10][CH:11]=1)[CH:13]([CH3:15])[CH3:14]Participants
4
Conditions
- Temperature
- 115 °C
Procedure
Triethylorthoacetate (15.4 mL, 84.2 mmol) was added slowly to a solution of isobutyl benzoic acid (5.0 g, 28.1 mmol) and toluene (60 mL) at room temperature. The resulting heterogeneous solution was heated to 115° C. and stirred for 24 hours. The reaction mixture was cooled to room temperature and quenched with 1N HCl (60 mL). The organic layer was separated, washed with saturated NaHCO3 (1×30 mL) and brine (1×30 mL), dried (MgSO4), filtered and concentrated in vacuo to obtain the title compound (5.59 g, 97% yield) as a clear oil.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- customquenched with 1N HCl (60 mL)
- customThe organic layer was separated
- washwashed with saturated NaHCO3 (1×30 mL) and brine (1×30 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-717be8cf6125499bb8c5c7f76a753a8f
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07671043B2
Reaction notes
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