Ethanol → HCID 18319055, compound

HRID 1383948Notes

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-f78c4ce687624e7bab6490cde664ad1f
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255496B1

Reaction notes

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