Hydrochloric Acid → 4-[6-(2,3-Dihydroxyphenyl)hexyloxy]-alpha-oxobenzeneacetic acid

HRID 2225823Notes

Reaction equation

C1(C[O:8][C:9]2[C:14]([O:15]CC3C=CC=CC=3)=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36](=[O:40])[C:37]([OH:39])=[O:38])=[CH:32][CH:31]=2)C=CC=CC=1.Cl>C(O)(=O)C.O>[OH:8][C:9]1[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:31]=[CH:32][C:33]([C:36](=[O:40])[C:37]([OH:39])=[O:38])=[CH:34][CH:35]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-[6-[2,3-bis-(phenylmethoxy)phenyl]hexyloxy]-alpha-oxobenzeneacetic acid (0.3 g) in acetic acid (20 mL) containing concentrated hydrochloric acid (5 mL) was stirred at 80° C. for 2.5 hours. The cooled solution was diluted with water (100 mL) and extracted with three portions of ethyl acetate, then the combined extracts were dried (Na2SO4), and evaporated in vacuo. The residual oil was triturated in turn with cyclohexane and carbon tetrachloride to remove non polar impurities, then was crystallized from dichloromethane and recrystallized from dichloromethane-carbon tetrachloride to give 4-[6-(2,3-dihydroxyphenyl)hexyloxy]-alpha-oxobenzeneacetic acid as a colorless solid, mp 127°-130° C.

Workup

extractionextracted with three portions of ethyl acetate
dry with materialthe combined extracts were dried (Na2SO4)
customevaporated in vacuo
customThe residual oil was triturated in turn with cyclohexane and carbon tetrachloride
customto remove non polar impurities
customwas crystallized from dichloromethane
customrecrystallized from dichloromethane-carbon tetrachloride

Sources & evidence

ORD record: ord-12e51b83ce3e4bf99d15bb06e19008c1
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05344843

Reaction notes

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