(+-)-Methionine → 3'-Hydroxy-[1,1'-biphenyl]-3-carboxylic acid

HRID 377311Notes

Reaction equation

HRID 377311 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.NC(C(O)=O)CCSC>CS(O)(=O)=O.O>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 876(+-)-MethionineHCID 27595503'-Methoxy-biphenyl-3-carboxylic acid

Product 1

HCID 27593013'-Hydroxy-[1,1'-biphenyl]-3-carboxylic acidYield 93.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6395Methanesulfonic AcidSolvent

Procedure

A suspension of 3'-methoxy-3-biphenylcarboxylic acid (4.1 g) and DL-methionine (26.7 g) in methanesulfonic acid (116 ml) was stirred at room temperature for 22 hours, diluted with water, and extracted three times with diethyl ether. The extracts were combined, washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was crystallized from n-hexane to afford 3'-hydroxy-3-biphenylcarboxylic acid (3.59 g) as a colorless powder.

Workup

  1. extractionextracted three times with diethyl ether
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-912e2197e69c4bb7a28b8e9c6f6a6ac3
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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