Acetyl chloride → [4-(4-Acetyl-phenyl)-cyclohexyl]-acetic acid ethyl ester

HRID 76071Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH3:2].[Cl-].[Cl-].[Cl-].[Al+3].[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[CH2:7][CH2:8][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:23](=[O:25])[CH3:24])=[CH:14][CH:13]=2)[CH2:10][CH2:11]1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of (4-phenyl-cyclohexyl)-acetic acid ethyl ester (15 g, 61 mmol, 1.0 equiv) in 200 Ml DCM was added aluminum trichloride (16 g, 122 mmol, 2.0 equiv) portionwise over 15 min. Acetyl chloride (4.7 Ml, 67 mmol, 1.10 equiv) was then added dropwise via syringe. The homogeneous solution was allowed to stir at 0° C. for 2 h, then carefully quenched with 300 Ml ice water. The mixture was extracted with DCM (3×150 Ml), and the organic extracts were washed with saturated bicarbonate and brine solution. Removal of solvent in vacuo afforded the title compound: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.10 (q, J=11.96 Hz, 2H) 1.20 (t, J=7.20 Hz, 3H) 1.40-1.51 (m, 2H) 1.84 (d, J=11.12 Hz, 4H) 1.76-1.87 (m, 1H) 2.17 (d, J=6.82 Hz, 2H) 2.50 (s, 3H) 4.07 (q, J=7.07 Hz, 2H) 7.22 (d, J=8.34 Hz, 2H) 7.81 (d, J=8.08 Hz, 2H); (M+H)+289.1.

Workup

customcarefully quenched with 300 Ml ice water
extractionThe mixture was extracted with DCM (3×150 Ml)
washthe organic extracts were washed with saturated bicarbonate and brine solution
customRemoval of solvent in vacuo

Sources & evidence

ORD record: ord-98c0374222c0445883ec0d377f36b77f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835451B2

Reaction notes

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