Methanol → 3-Methyl-5-phenylbenzoic acid

HRID 2228018Notes

Reaction equation

HRID 2228018 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH3:15])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)#N.[OH-:16].[K+].C[OH:19]>O>[CH3:15][C:5]1[CH:4]=[C:3]([CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=1)[C:1]([OH:19])=[O:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 184745443-Cyano-5-phenyltoluene

Product 1

HCID 184745993-Methyl-5-phenylbenzoic acidYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-cyano-5-phenyltoluene (5.06 g; 26 mmol) and potassium hydroxide (2.94 g; 52 mmol) in methanol (40 ml) and water (60 ml) was refluxed for 24 hours. After evaporation of the methanol and filtration of the unsoluble material, the mixture was acidified to pH 2 with 6N HCl. The resulting precipitate was filtered, washed with water and dried to give 3-methyl-5-phenylbenzoic acid. Yield=65%.

Workup

  1. customAfter evaporation of the methanol and filtration of the unsoluble material
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-ba4720a959a249e999ee0e368d160bec
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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