Phenol → 1-(4-Hydroxyphenyl)-2-(4-methoxyphenyl)ethanone

HRID 1776271Notes

Reaction equation

HRID 1776271 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([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[OH: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

3

Reactant 2

HCID 996PhenolHCID 76904-Methoxyphenylacetic Acid

Product 1

HCID 126053601-(4-Hydroxyphenyl)-2-(4-methoxyphenyl)ethanoneYield 20.6%

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(4-methoxyphenyl)acetic acid (10 g, 0.06 mol) in PPA (20 mL) was added dropwise phenol (5.6 g, 0.06 mol) under an inert atmosphere. The mixture was then stirred at 80° C. for 1 h, quenched with cold water and extracted with EtOAc (2×300 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to obtain the crude product which was purified via silica gel column chromatography to afford 1-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-ethanone (3 g, 20%) as a pale yellow solid

Workup

  1. customquenched with cold water
  2. extractionextracted with EtOAc (2×300 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto obtain the crude product which
  6. customwas purified via silica gel column chromatography

Sources & evidence

ORD record
ord-b4a7a32ef1d34f0ab1559f30f3ad4608
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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