Phthalic Anhydride → HCID 765165, compound

HRID 849165Notes

Reaction equation

HRID 849165 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:20])=[CH:17][C:18]=1[OH:19]>C(O)(=O)C>[OH:19][C:18]1[CH:17]=[C:16]([CH3:20])[CH:15]=[CH:14][C:13]=1[N:12]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 760822-Amino-5-methylphenol

Product 1

HCID 765165HCID 765165, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of phthalic anhydride (14.81 g, 0.10 mole) and 6-amino-m-cresol (12.32 g, 0.10 mole) in 200 mL of acetic acid was stirred at ambient temperature for 30 minutes and then refluxed for 6 hours. The solution was cooled and poured into 500 mL ice-water with rapid stirring and the resultant solid was collected by suction filtration, washed with ice-cold water several times and air dried overnight to afford 24.1 g (95% yield) of product 1 as a light brown solid, mp 251-254° C. TLC (silica ; EtOAc), Rf=0.68.

Workup

  1. temperaturerefluxed for 6 hours
  2. temperatureThe solution was cooled
  3. filtrationthe resultant solid was collected by suction filtration
  4. washwashed with ice-cold water several times and air
  5. customdried overnight

Sources & evidence

ORD record
ord-009e156982d04d078e8d6a773f750a5a
Source dataset
uspto-grants-2000_01
Patent number
US06011047

Reaction notes

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