Methanol → Methyl 4'-hydroxy-2',6'-dimethyl-6-(phenoxymethyl)biphenyl-3-carboxylate

HRID 416178Notes

Reaction equation

COC[O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([C:12]2[C:17]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=[C:14]([C:26]([O:28][CH3:29])=[O:27])[CH:13]=2)=[C:7]([CH3:30])[CH:6]=1.CO.Cl.CO>C(COC)OC>[OH:4][C:5]1[CH:6]=[C:7]([CH3:30])[C:8]([C:12]2[C:17]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=[C:14]([C:26]([O:28][CH3:29])=[O:27])[CH:13]=2)=[C:9]([CH3:11])[CH:10]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of methyl 4′-(methoxymethoxy)-2′,6′-dimethyl-6-(phenoxymethyl)biphenyl-3-carboxylate (1.77 g, 4.35 mmol) in a mixed solvent of methanol (10 mL) and dimethoxyethane (5 mL) was added 10% hydrogen chloride-methanol solution (1 mL), and the mixture was stirred at 45° C. for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-25:75) to give the title compound (1.47 g, yield 93%) as a colorless amorphous powder.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-25:75)

Sources & evidence

ORD record: ord-d2e5fd64497146209fab2d96c99a71a0
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088821B2

Reaction notes

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