Diphenyl Ether → HCID 57209852, compound

HRID 580982Notes

Reaction equation

C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:7][CH:6]=1)C=C.[C:18]1(OC2C=CC=CC=2)[CH:23]=CC=C[CH:19]=1>>[CH2:23]([C:10]1[CH:9]=[C:8]([CH2:11][O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:7]=[CH:6][C:5]=1[OH:4])[CH:18]=[CH2:19]

Participants

Reactant 2

HCID 7583Diphenyl Ether

HCID 53797859HCID 53797859, compound

Product 1

HCID 57209852HCID 57209852, compound

Conditions

Temperature: 200 °C

Procedure

A mixture of methyl 4-allyloxyphenylmethyloxyacetate (2.00 g) and diphenyl ether (14 ml) was heated at 200° C. in an atmosphere of argon for 9 hours. The mixture was cooled to ambient temperature and purified by flash column chromatography on silica gel using a 4:1 (v/v) mixture of hexane and ethyl acetate as eluent to give methyl (3-allyl-4-hydroxyphenyl)methyloxyacetate (435 mg) as a colourless oil; NMR(CDCl3): 3.38(2H,d), 3.75(3H,s), 4.07(2H,s), 4.52(2H,s), 5.12(2H,m), 6.00(1H,m), 6.78(1H,m) and 7.08(2H,m); m/z 236(M).

Workup

temperatureThe mixture was cooled to ambient temperature
custompurified by flash column chromatography on silica gel using
additiona 4:1 (v/v) mixture of hexane and ethyl acetate as eluent

Sources & evidence

ORD record: ord-c9bd79c1b6ae42a08d1d228cc8371ce2
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05919793

Reaction notes

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