Potassium Carbonate → Benzyl 3-(1-acetyl-2-oxocyclohexyl)propanoate

HRID 1957455Notes

Reaction equation

[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:10])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:17]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:20])[CH:18]=[CH2:19]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[C:1]([C:4]1([CH2:19][CH2:18][C:17]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:10])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2-acetylcyclohexanone (9.6 g, 0.068 mol), potassium carbonate (11.3 g, 0.082 mol) and benzyltriethylammonium chloride (0.3 g, 0.0013 mol) in toluene (26 ml), was added benzyl acrylate (16.72 g, 0.103 mol) at room temperature. The mixture was heated at 40° C. for 20 hours, cooled, partitioned between water (200 ml) and toluene (200 ml) and toluene (200 ml) and the layers separated. The aqueous layer was extracted with toluene (2×200 ml), the combined organic extracts dried over magnesium sulphate, filtered and concentrated under reduced pressure to provide the title compound as a pale yellow oil, (20.7 g), Rf. 0.2 (silica, hexane/diethyl ether, 2:1). The crude product was used without further purification.

Workup

temperaturecooled
custompartitioned between water (200 ml) and toluene (200 ml) and toluene (200 ml)
customthe layers separated
extractionThe aqueous layer was extracted with toluene (2×200 ml)
dry with materialthe combined organic extracts dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f793007c5f40411f8232c7df0a0d6a52
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE035865

Reaction notes

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