Potassium Hydroxide → 4-[2-[4'-Fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-yloxy]ethoxy]-alpha-oxobenzeneacetic acid

HRID 2225799Notes

Reaction equation

HRID 2225799 reaction equation
C[O:2][C:3](=[O:32])[C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[C:20]([CH:21]([CH3:23])[CH3:22])=[CH:19][CH:18]=[CH:17][C:16]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:7][CH:6]=1.[OH-].[K+]>CO.O1CCCC1>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([CH:21]([CH3:23])[CH3:22])[C:15]=2[O:14][CH2:13][CH2:12][O:11][C:8]2[CH:7]=[CH:6][C:5]([C:4](=[O:31])[C:3]([OH:32])=[O:2])=[CH:10][CH:9]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 545175004-[2-[4'-Fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-yloxy]ethoxy]-alpha-oxobenzeneacetic acid methyl ester

Product 1

HCID 190043724-[2-[4'-Fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-yloxy]ethoxy]-alpha-oxobenzeneacetic acidYield 66.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

As in Example 19, 4-[2-[4'-fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-yloxy]ethoxy]-alpha-oxobenzeneacetic acid methyl ester (0.186 g) in a mixture of methanol (2 mL) and tetrahydrofuran (1 mL) was treated with 1N potassium hydroxide (0.52 mL). The usual work up gave 0.17 g of a solid, which after crystallization from diethyl ether-hexane afforded 0.12 g of 4-[2-[4'-fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-yloxy]ethoxy]-alpha-oxobenzeneacetic acid, mp 123°-125° C.

Workup

  1. customThe usual work up gave 0.17 g of a solid, which after crystallization from diethyl ether-hexane

Sources & evidence

ORD record
ord-9a239fe95d8e40e497c5a0b50555c652
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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