Water → HCID 22915470, compound

HRID 1377910Notes

Reaction equation

HRID 1377910 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=1.O.[OH-].[Na+]>CO>[C:15]1([C:11]2[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=2)[O:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:21])=[O:2])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 54381400HCID 54381400, compound

Product 1

HCID 22915470HCID 22915470, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution in methanol (7.5 mL) of 5-(3-phenylphenoxy)pentanoic acid methyl ester (1.42 g, 5.0 mmol), prepared as in step 1, was added water (3.75 mL) and aqueous 4N sodium hydroxide (3.75 mL). The reaction mixture was stirred for 3.5 hours and then was concentrated in vacuo. The residue was partitioned between water and ethyl ether. The aqueous phase was taken to pH 2 with concentrated HCl and extracted twice with ethyl acetate. The combined ethyl acetate extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give a white solid. Trituration of the solid with 1:1 ethyl ether-hexanes gave 5-(3-phenylphenoxy)pentanoic acid (1.21 g) as a white powder.

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe residue was partitioned between water and ethyl ether
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe combined ethyl acetate extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a white solid

Sources & evidence

ORD record
ord-11016aaf22724985beb0bf05cd12ae23
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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