Acetic Acid → 2-isopropylidene-1-indanone
Reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[K+].C(O)(=O)C.[CH3:17][C:18]([CH3:20])=O>>[C:18](=[C:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]1=[O:10])([CH3:20])[CH3:17]Participants
Procedure
To a solution of 1-indanone (120 g, 0.908 mole) in acetone (180 g) inside of 500 mL round-bottom flask was added 9 mL of ethanolic potassium hydroxide (3 g, 0.054 mole) solution. The solution was heated under reflux for 7.5 hours and then acidified with acetic acid. Volatile components were removed by a rotary evaporator. To the residue diethyl ether (200 mL) and water (100 mL) were added. The aqueous layer was extracted with diethyl ether (4*200 mL). All etheral layers were combined, washed with water (50 mL), dried over anhydrous magnesium sulfate and concentrated to yield 152 g of crude product. Fractional distillation (80 to 120° C./0.3 mmHg) and recrystallization from methanol yielded 29 g of 2-isopropylidene-1-indanone. H-NMR (CDCl3) δ 1.99 (s, 3 H), 2.43 (s, 3 H), 3.62 (s, 2 H), 7.36 (br t, J=7.6 Hz, 1 H), 7.45 (br d, J=7.6 Hz, 1 H), 7.53 (td, J=7.6, 1.2 Hz, 1H), 7.80 (br d, J=7.6 Hz, 1H).
Workup
- temperatureThe solution was heated
- temperatureunder reflux for 7.5 hours
- customVolatile components were removed by a rotary evaporator
- additionTo the residue diethyl ether (200 mL) and water (100 mL) were added
- extractionThe aqueous layer was extracted with diethyl ether (4*200 mL)
- washwashed with water (50 mL)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customto yield 152 g of crude product
- distillationFractional distillation (80 to 120° C./0.3 mmHg) and recrystallization from methanol
Sources & evidence
- ORD record
- ord-6479530c41fa4dc1b109467fecdb798f
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06391991B1
Reaction notes
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