Water → 4-[2-(Benzyloxy)-4-ethylphenoxy]-3-fluorophenol

HRID 1023971Notes

Reaction equation

C([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][C:13]=2[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:7]([F:28])[CH:6]=1)(=O)C.O.[OH-].[K+]>CO>[CH2:21]([O:20][C:13]1[CH:14]=[C:15]([CH2:18][CH3:19])[CH:16]=[CH:17][C:12]=1[O:11][C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][C:7]=1[F:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 4-[2-(benzyloxy)-4-ethylphenoxy]-3-fluorophenyl acetate (1.6 g, 4.2 mmol) in MeOH:H2O (35 ml:35 ml), was added KOH (0.83 g, 14.8 mmol). The mixture was heated at 65° C. for 4.5 hours, concentrated in vacuo, then extracted with EtOAC (25 ml*2). Combined organic phases were dried over Na2SO4 and concentrated. The residue was purified by column chromatography, (pet ether: EtOAC 95:5), to yield the title compound as a white solid (630 mg; 44%)

Workup

concentrationconcentrated in vacuo
extractionextracted with EtOAC (25 ml*2)
dry with materialCombined organic phases were dried over Na2SO4
concentrationconcentrated
customThe residue was purified by column chromatography, (pet ether: EtOAC 95:5),

Sources & evidence

ORD record: ord-a75e915a734c4add9da72beaf54a6fd8
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722746B2

Reaction notes

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