Phenol → 2-Naphthalenecarboxylic acid, 3-hydroxy-, phenyl ester

HRID 972425Notes

Reaction equation

[OH:1][C:2]1[C:3]([C:12]([OH:14])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:15]1(O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.P(Cl)(Cl)(Cl)=O>>[C:15]1([O:13][C:12]([C:3]2[C:2]([OH:1])=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=2)=[O:14])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Reactant 3

HCID 996Phenol

HCID 71043-Hydroxy-2-naphthoic acid

HCID 24813Phosphorus oxychloride

Product 1

HCID 816802-Naphthalenecarboxylic acid, 3-hydroxy-, phenyl esterYield 38%

Conditions

Temperature: 100 °C

Procedure

A mixture of 50 g (0.266 mole) 3-hydroxy-2-naphthoic acid, 27.3 g (0.29 mole) phenol, and 21.4 g (0.14 mole) phosphorus oxychloride was stirred and heated at 100° C. for 3.5 hrs. Then 200 ml alcohol was added, and the mixture was heated one hour longer and cooled. The yellow product was collected and recrystallized from benzene to give 26.4 g (38%) of phenyl-3-hydroxy-2-naphthoate, m.p. 126°-130° C.

Workup

temperaturethe mixture was heated one hour longer
temperaturecooled
customThe yellow product was collected
customrecrystallized from benzene

Sources & evidence

ORD record: ord-1aa586862b984cd280dddaef64c981fa
Source dataset: uspto-grants-1977_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04053312

Reaction notes

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