Potassium Carbonate → 2-Acetyl-2-[2-(tert-butoxycarbonyl)ethyl]cyclohexanone

HRID 374341Notes

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][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])[CH:18]=[CH2:19].CCCCCC.C(OCC)(=O)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1.O>[C:1]([C:4]1([CH2:19][CH2:18][C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[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 suspension of 2-acetylcyclohexanone (100 g, 0.71 mol), potassium carbonate (118.3 g, 0.85 mol) and benzyltriethylammonium chloride (3.18 g, 0.014 mol) in toluene (280 ml), was added, in one portion, tert-butyl acrylate (137.1 g, 155.2 ml, 1.07 mol) at room temperature. The suspension was stirred at 40° C. for 18 hours, diluted with distilled water (1 L) and toluene (500 ml), and the layers separated. The aqueous layer was extracted with toluene (3×500 ml), the combined toluene extracts dried over magnesium sulphate, filtered and concentrated under reduced pressure to give a brown oil, (197.8 g) Rf. 0.41 (silica, hexane/ethyl acetate, 3:1). The crude product was used without further purification.

Workup

customthe layers separated
extractionThe aqueous layer was extracted with toluene (3×500 ml)
dry with materialthe combined toluene extracts dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give a brown oil, (197.8 g) Rf
customThe crude product was used without further purification

Sources & evidence

ORD record: ord-820442fe3b7f44158fef658ddfdab54d
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05166406

Reaction notes

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