Aluminum(III) Chloride → 2'-Cyclohexyl-5'-hydroxy-4'-methoxyacetophenone

HRID 41945Notes

Reaction equation

[CH:1]1([C:7]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15]C(C)C)=[CH:9][C:8]=2[C:19](=[O:21])[CH3:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH:1]1([C:7]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([OH:15])=[CH:9][C:8]=2[C:19](=[O:21])[CH3:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 18 °C

Procedure

A solution of ketone 52 (50 mg, 0.172 mmol) in dry CH2Cl2 (1.5 mL) was treated with AlCl3 (0.069 mg, 0.517 mmol) and the resulting mixture stirred magnetically at 18° C. under a nitrogen atmosphere for 2.5 h then partitioned between H2O (10 mL) and CH2Cl2 (10 mL). The separated aqueous phase was extracted with CH2Cl2 (1×10 mL) and the combined organic fractions dried (MgSO4), filtered and concentrated, under reduced pressure, onto TLC-grade silica (ca. 80 mg). The resulting free-flowing solid was subjected to flash chromatography (1:19→15:85 v/v ethyl acetate/hexane gradient elution) to afford the title compound 53 (31 mg, 72%) as a colourless oil, Rf 0.6 in 1:1 v/v ethyl acetate/hexane.

Workup

customthen partitioned between H2O (10 mL) and CH2Cl2 (10 mL)
extractionThe separated aqueous phase was extracted with CH2Cl2 (1×10 mL)
dry with materialthe combined organic fractions dried (MgSO4)
filtrationfiltered
concentrationconcentrated, under reduced pressure, onto TLC-grade silica (ca. 80 mg)
washThe resulting free-flowing solid was subjected to flash chromatography (1:19→15:85 v/v ethyl acetate/hexane gradient elution)

Sources & evidence

ORD record: ord-e1810f5a89e845939225c6229939fa19
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536157B2

Reaction notes

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