Hydroxyphenylacetic acid → 1-(2-Hydroxy-4-methoxyphenyl)-2-(4-hydroxyphenyl)ethanone

HRID 1296685Notes

Reaction equation

HRID 1296685 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[OH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18](O)=[O:19])=[CH:13][CH:12]=1.B(F)(F)F.CCOCC>ClC1C=CC=CC=1>[OH:9][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[C:18](=[O:19])[CH2:17][C:14]1[CH:15]=[CH:16][C:11]([OH:10])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 8000Boron trifluoride etherateHCID 90073-Methoxyphenol

Product 1

HCID 149200561-(2-Hydroxy-4-methoxyphenyl)-2-(4-hydroxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
7.5 °C

Procedure

A suspension of 3-methoxyphenol (44.69 kg, 360 mol) and 4-hydroxyphenylacetic acid (68.5 kg, 450 mol) in 144 L of chlorobenzene was purged with nitrogen gas. Boron trifluoride diethyl etherate (177 L, 1440 mol) was added at 20 to 25° C. The resultant suspension was heated to 80° C., stirred for 4 to 5 h, cooled to 5 to 10° C. and stirred overnight.

Workup

  1. customwas purged with nitrogen gas
  2. stirringstirred overnight

Sources & evidence

ORD record
ord-8e508067939f4ac5a45a7ebddbf1c416
Source dataset
uspto-grants-2007_07
Patent number
US07247646B2

Reaction notes

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