Hydrochloric Acid → (2E)-3-{4-[Cyclohexylidene(4-hydroxy-2-methylphenyl)methyl]phenyl}-2-propenoic acid

HRID 229152Notes

Reaction equation

[C:1]1(=[C:7]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=2[CH3:28])[C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([O:18]CC)=[O:17])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>CCO.C1COCC1>[C:1]1(=[C:7]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=2[CH3:28])[C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([OH:18])=[O:17])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of ethyl (2E)-3-{4-[cyclohexylidene(4-hydroxy-2-methylphenyl)methyl]phenyl}-2-propenoate (30) (0.42 g, 1.11 mmol) in a mixture of EtOH/THF (1 mL, 4 mL) was added an aqueous solution of 5M NaOH (1.4 mL, 7.00 mmol). The mixture was stirred at 85° C. for 4 h. Upon cooling, the mixture was acidified to pH=2 with an aqueous solution of 5 M HCl. The mixture was extracted with EtOAc (1×20 mL). The organics were washed with water and brine (1×10 mL each) and dried with MgSO4. Concentration yielded 0.39 g (100%) of compound 31. 1H NMR (400 MHz, DMSO-d6): δ 1.46-1.58 (m, 6H), 1.91-1.96 (m, 2H), 1.97 (s, 3H), 2.22-2.26 (m, 2H), 6.43 (d, J=16.1 Hz, 1H), 6.53 (m, 2H), 6.83-6.85 (m, 1H), 7.08 (d, J=8.1 Hz, 2H), 7.50 (d, J=16.2 Hz, 1H), 7.55 (d, J=8.1 Hz, 2H), 9.16 (s, 1H), 12.32 (s, 1H). LCMS (ESI): m/z 349 (M+H)+.

Workup

temperatureUpon cooling
extractionThe mixture was extracted with EtOAc (1×20 mL)
washThe organics were washed with water and brine (1×10 mL each)
dry with materialdried with MgSO4
concentrationConcentration

Sources & evidence

ORD record: ord-1f6cd8ee35d04577942db09b919de06a
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560589B2

Reaction notes

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