Ethanol → HCID 18319055, compound

HRID 1700935Notes

Reaction equation

C[O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][S:15][CH2:16][CH2:17][O:18][CH:19]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[CH:8][CH:7]=1.C(O)C.[OH-].[K+]>O>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH:19]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[O:18][CH2:17][CH2:16][S:15][CH2:14][CH2:13][O:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:34])=[O:2])=[CH:7][CH:8]=2)=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-[4-[2-[2-[Bis(4-chlorophenyl]methoxy]ethylthio]ethoxy]phenyl]propionic acid methyl ester (2.76 g, 5.31 mmol) and 80% aqueous ethanol (50 ml) was treated with a solution of potassium hydroxide (0.7 g, 10.6 mmol) in water (3 ml) and the resulting mixture was heated at 60° C. for 1 h. The solvent was then concentrated in vacuo and the residue was diluted with water (30 ml) and dichloromethane (50 ml) and acidified to pH4 with 2N hydrochloric acid. The aqueous phase was extracted a second time with dichloromethane and the combined organic extracts were washed with brine and dried (magnesium sulfate). Evaporation of the solvent under reduced pressure gave 2.63 g (98%) of the title acid as a white solid.

Workup

concentrationThe solvent was then concentrated in vacuo
additionthe residue was diluted with water (30 ml) and dichloromethane (50 ml)
extractionThe aqueous phase was extracted a second time with dichloromethane
washthe combined organic extracts were washed with brine
dry with materialdried (magnesium sulfate)
customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record: ord-caff024028374511b231aa9a80d55b07
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350892B1

Reaction notes

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