2,2-Dimethoxypropane → 3-(4-Bromo-benzoyl)cyclohexanecarboxylic acid methyl ester

HRID 30878

Reaction equation

[Br:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C@H:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([OH:16])=[O:15])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[CH3:19]OC(OC)(C)C>CO.Cl.O1CCOCC1>[CH3:19][O:15][C:14]([CH:10]1[CH2:11][CH2:12][CH2:13][CH:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:18][CH:17]=2)[CH2:9]1)=[O:16]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of trans-3-(4-bromobenzoyl)cyclohexane-l-carboxylic acid (500 mg, 1.61 mmol, obtained from Rieke Metals Inc., Lincoln, Nebr., USA) and 2,2-dimethoxypropane (669 mg, 6.43 mmol) in methanol (20 mL), 5 drops of 4 M HCl in dioxane was added, and this reaction mixture was heated at 50° C. overnight. The solvent was removed by rotary evaporation to give the product 3-(4-bromo-benzoyl)-cyclohexanecarboxylic acid methyl ester as a brown oil (500 mg, yield 95.7%). 1H NMR (300 MHz, DMSO) δ 7.80 (d, 2H), 7.60 (d, 2H), 3.70 (s, 3H), 3.25 (m, 1 H), 2.50 (m, 1H), 2.20-1.90 (m, 4H), 1.70-1.50 (m, 4H); LC-MS ret. time 3.30 min, m/z 324.9 (MH+).

Workup

customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record: ord-a3cae5db62c946899d7feda72e6ef962
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423156B2

Linked notes

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