Hydrochloric Acid → 2-Isopropoxybenzoic acid
Reaction equation
[CH:1]([O:4][C:5]1[CH:16]=[CH:15][CH:14]=[CH:13][C:6]=1[C:7]([O:9]C(C)C)=[O:8])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].CCCCCC.C(OCC)(=O)C.Cl>CS(C)=O>[CH:1]([O:4][C:5]1[CH:16]=[CH:15][CH:14]=[CH:13][C:6]=1[C:7]([OH:9])=[O:8])([CH3:3])[CH3:2]Participants
6
Conditions
- Temperature
- 70 °C
Procedure
To a stirred solution of Isopropyl 2-isopropoxy-benzoate (10 g, 240 mmol) in dimethyl sulfoxide (40 mL) was added potassium tert-butoxide (10 g, 890 mmol) in portions. The solution was heated to 70° C. on a water bath for 2 h, and the progress of the reaction was monitored by TLC using a hexane-ethyl acetate (8:2) solvent system. The reaction mass was cooled to 10° C., poured into ice water, and then acidified with 5% dilute hydrochloric acid. The precipitated solid was filtered and washed thoroughly with distilled water, and the crude mass was recrystallized in hexane (50 mL) to yield an off-white solid of 2-Isopropoxy-benzoic Acid (7.6 g, 80%).
Workup
- temperatureThe reaction mass was cooled to 10° C.
- filtrationThe precipitated solid was filtered
- washwashed thoroughly with distilled water
- customthe crude mass was recrystallized in hexane (50 mL)
Sources & evidence
- ORD record
- ord-cca77733234848db8138878ec42d0426
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07332629B2
Reaction notes
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