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Methanol → 5-(3-Chloro-benzoylamino)-2-phenoxy-benzoic acid

HRID 1967646
Notes
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Reaction equation

HRID 1967646 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([NH:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[CH:7]=[CH:6][C:5]=1[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CO.O.O.[OH-].[Li+]>O1CCCC1>[Cl:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[C:11]([NH:10][C:8]1[CH:7]=[CH:6][C:5]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:4]([CH:9]=1)[C:3]([OH:27])=[O:2])=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 592023865-(3-Chloro-benzoylamino)-2-phenoxy-benzoic acid methyl ester

Product 1

HCID 592023805-(3-Chloro-benzoylamino)-2-phenoxy-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

5-(3-Chloro-benzoylamino)-2-phenoxy-benzoic acid methyl ester (1.56 g, 4.00 mmol) (see Example I1) was dissolved in a mixture of tetrahydrofuran (15 ml), methanol (1.5 ml), and water (1.5 ml). Lithium hydroxide monohydrate (336 mg, 8 mmol) was added and the reaction mixture stirred at ambient temperature for 3 days. The reaction mixture was concentrated and the residue extracted with water and tert-butyl-methyl-ether. The aqueous phase was acidified by the addition of a few drops of concentrated hydrochloric acid and extracted with ethyl acetate. The phases were separated, the organic phase was dried over sodium sulfate and concentrated. The residue was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe residue extracted with water and tert-butyl-methyl-ether
  3. additionThe aqueous phase was acidified by the addition of a few drops of concentrated hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. customThe phases were separated
  6. dry with materialthe organic phase was dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was used without further purification

Sources & evidence

ORD record
ord-69d1285ae438474e930e547087e95976
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08420855B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes