Anisole → Desoxyanisoin

HRID 2205124Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.[C:13]1([O:19][CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH3:20][O:19][C:13]1[CH:18]=[CH:17][C:16]([C:10](=[O:12])[CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:15][CH:14]=1

Participants

Reactant 2

HCID 7519Anisole

HCID 76904-Methoxyphenylacetic Acid

Product 1

HCID 67120DesoxyanisoinYield 52%

Procedure

The diaryl product was obtained using the same synthetic methods as shown in Example 25, step 5, using 2-(4-methoxyphenyl)acetic acid (5.0 g, 30.1 mmol, 1.00 equiv) and anisole (16 g, 148.1 mmol, 5.00 equiv) as reactants. Purification via silica gel column (ethyl acetate/petroleum ether (1:10)) afforded 4.0 g (52%) of 1,2-bis(4-methoxyphenyl)ethanone as a white solid.

Workup

customPurification via silica gel column (ethyl acetate/petroleum ether (1:10))

Sources & evidence

ORD record: ord-5f5e2c8fe33641a0a6d91e7d0e3e51e1
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09370522B2

Reaction notes

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