HCID 66818173, compound → HCID 66817920, compound

HRID 1755035Notes

Reaction equation

C([O:8][C:9](=[O:23])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[CH:12][CH:11]=1)C1C=CC=CC=1.[H][H]>CC(O)C>[F:20][C:19]([F:21])([F:22])[CH2:18][CH2:17][O:16][CH:13]1[CH2:12][CH2:11][CH:10]([C:9]([OH:23])=[O:8])[CH2:15][CH2:14]1

Participants

Conditions

Temperature: 80 °C

Procedure

10% Rh—C (14.7 mg) was added to a solution of 4-(3,3,3-trifluoro-propoxy)-benzoic acid benzyl ester (147.3 mg, 0.454 mmol) in iPrOH (1.5 mL). The hydrogen pressure was adjusted to 5 atm, and the mixture was then heated with stirring at 80° C. overnight. The reaction mixture was filtered through celite, and the filtrate was then diluted with ethyl acetate. A saturated aqueous sodium bicarbonate solution was added, and the organic layer and the aqueous layer were separated. The aqueous layer was adjusted to pH 1 with 1 N hydrochloric acid and then extracted with ethyl acetate. The organic layers were sequentially washed with water and saturated brine, and then dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 4-(3,3,3-trifluoro-propoxy)-cyclohexanecarboxylic acid as a colorless transparent oily substance (70.2 mg, 64%).

Workup

temperaturethe mixture was then heated
filtrationThe reaction mixture was filtered through celite
additionthe filtrate was then diluted with ethyl acetate
additionA saturated aqueous sodium bicarbonate solution was added
customthe organic layer and the aqueous layer were separated
extractionextracted with ethyl acetate
washThe organic layers were sequentially washed with water and saturated brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3f926aac66ad41d1b8612280ad38d1f4
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169254B2

Reaction notes

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