Hydrochloric Acid → 4-[1-Allyl-1-(2,6-dimethyl-4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoic acid

HRID 658297Notes

Reaction equation

C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:34][CH:35]=[CH2:36])([CH2:14][O:15][C:16]2[CH:21]=[C:20]([CH3:22])[C:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[C:18]([CH3:33])[CH:17]=2)[CH2:11][CH:12]=[CH2:13])=[CH:6][CH:5]=1.[Li+].[OH-].Cl>C1COCC1>[CH2:11]([C:10]([C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:37])=[O:2])=[CH:9][CH:8]=1)([CH2:14][O:15][C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][CH:24]=2)=[C:18]([CH3:33])[CH:17]=1)[CH2:34][CH:35]=[CH2:36])[CH:12]=[CH2:13]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 4-[1-allyl-1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoic acid methyl ester (0.386 g, 0.758 mmol) in THF (8.0 mL) is treated with 1N LiOH (8.0 mL, 8.0 mmol), warmed to 70° C., and stirred overnight. The reaction mixture is cooled to room temperature, acidified with 1N HCl (9.0 mL), and extracted with EtOAc (3×20 mL). The combined extracts are dried over MgSO4, filtered, and concentrated to provide 0.356 g (95%) of the title compound as a white foam. MS (ES): 493.3 [M−H]−.

Workup

temperatureThe reaction mixture is cooled to room temperature
extractionextracted with EtOAc (3×20 mL)
dry with materialThe combined extracts are dried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-d4fe546a8eaa4ddbae659d178d33d9ad
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076374B2

Reaction notes

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