Methanol → Methyl 3-methyl-5-phenylbenzoate

HRID 2228019Notes

Reaction equation

HRID 2228019 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:17]O>OS(O)(=O)=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:10]=1)[C:5]([O:7][CH3:17])=[O:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 184745993-Methyl-5-phenylbenzoic acid

Product 1

HCID 11379139Methyl 3-methyl-5-phenylbenzoateYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of 3-methyl-5-phenylbenzoic acid (3.5 g; 16.5 mmol) and concentrated H2SO4 (30 drops) in methanol (25 ml) was heated at reflux overnight. After evaporation to dryness, the residue was extracted with ether. The organic phase was evaporated and purified by flash chromatography eluting with petroleum ether/ethyl acetate (90/10) to give methyl 3-methyl-5-phenylbenzoate as an oil. Yield=94%.

Workup

  1. temperatureat reflux overnight
  2. customAfter evaporation to dryness
  3. extractionthe residue was extracted with ether
  4. customThe organic phase was evaporated
  5. custompurified by flash chromatography
  6. washeluting with petroleum ether/ethyl acetate (90/10)

Sources & evidence

ORD record
ord-48ddedae0c894ffa8b2c2b9042f7762e
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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