Hydroxyphenylacetic acid → N-(3,5-dimethylphenyl)-2-(4-hydroxyphenyl)acetamide

HRID 1019411Notes

Reaction equation

HRID 1019411 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH3:12][C:13]1[CH:14]=[C:15]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[NH2:16]>C1(C)C(C)=CC=CC=1>[CH3:12][C:13]1[CH:14]=[C:15]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[NH:16][C:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)=[O:11]

Participants

4

Reactant 2

HCID 127Hydroxyphenylacetic acidHCID 79493,5-Dimethylaniline

Product 1

HCID 2763537N-(3,5-dimethylphenyl)-2-(4-hydroxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4-hydroxyphenylacetic acid (20.0 g, 131 mmol) and 3,5-dimethylaniline (15.9 g, 131 mmol) in xylene (100 mL) was stirred for three days at 160° C. with a Dean Stark trap. The mixture was cooled to room temperature and filtered. The solid product obtained was washed with hexane (200 mL), 10% sodium bicarbonate solution (250 mL), water (200 mL), 10% hydrochloric acid (200 mL), and then water (200 mL). The beige solid was air dried to yield 27.7 g, 82.7%. mp 183-185° C.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. customThe solid product obtained
  4. washwas washed with hexane (200 mL), 10% sodium bicarbonate solution (250 mL), water (200 mL), 10% hydrochloric acid (200 mL)
  5. customdried
  6. customto yield 27.7 g, 82.7%

Sources & evidence

ORD record
ord-f30b634dc5d442238ab064df5e621fd0
Source dataset
uspto-grants-2002_11
Patent number
US06486342B1

Reaction notes

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