Hydrochloric Acid → 2-(3-Hydroxyphenoxymethyl)-6-methylbenzoic Acid

HRID 731129Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:9](=[O:10])[O:8][CH2:7]2.[C:12]1([CH:19]=[CH:18][CH:17]=[C:15]([OH:16])[CH:14]=1)[OH:13].CC(C)([O-])C.[K+].Cl>CN1CCCC1=O.O>[OH:13][C:12]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[O:16][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH3:7])[C:11]=1[C:9]([OH:10])=[O:8]

Participants

Conditions

Temperature: 140 °C

Procedure

7-Methylphthalide (30.1 g, 203 mmol), resorcinol (45.3 g, 407 mmol) and potassium tert-butoxide (47.6 g, 424 mmol) are suspended in 300 ml of N-methylpyrrolidone (NMP) and stirred at 140° C. for 21 h. After this time, a second amount of potassium tert-butoxide (2.4 g, 21.4 mmol) is added and stirring is continued at 140° C. for 2.5 h. The reaction mixture is cooled, 800 ml of water are added, and the mixture is acidified to pH=2 at 20° C. with concentrated hydrochloric acid. After stirring at 3 to 5° C. for 2 hours, the pale beige solid is filtered off with suction, washed with water and then dried. The isolated product contains 2-(3-hydroxyphenoxymethyl)-6-methylbenzoic acid and N-methylpyrrolidone as solvate molecule in a ratio of 1:1. Yield 77.7%, melting point 98 to 99° C.

Workup

stirringstirring
waitis continued at 140° C. for 2.5 h
temperatureThe reaction mixture is cooled
stirringAfter stirring at 3 to 5° C. for 2 hours
filtrationthe pale beige solid is filtered off with suction
washwashed with water
customdried

Sources & evidence

ORD record: ord-b6f4f973b1b44949ae093f4986a5979a
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582794B2

Reaction notes

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