Methanol → Methyl 2-hydroxy-3-phenylbenzoate

HRID 1739475

Reaction equation

HRID 1739475 reaction equation
S(=O)(=O)(O)O.[OH:6][C:7]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:22]O>>[OH:6][C:7]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([O:11][CH3:22])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 93483-Phenylsalicylic acid

Product 1

HCID 241577Methyl 2-hydroxy-3-phenylbenzoate

Procedure

Methanol (50 ml) was treated with concentrated sulphuric acid (4.9 g, 2.66 ml) cautiously. 2-Hydroxy-3-phenylbenzoic acid (10.7 g, 50 mmol) was added and the reaction mixture stirred at ambient temperature for 18 hours. The mixture was then heated at reflux for 4 hours, cooled to ambient temperature and evaporated. The residue was partitioned between ethyl acetate/and water, the organic layer washed twice with water, dried (MgSO4) and evaporated to give methyl 2-hydroxy-3-phenylbenzoate.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 4 hours
  3. temperaturecooled to ambient temperature
  4. customevaporated
  5. customThe residue was partitioned between ethyl acetate/and water
  6. washthe organic layer washed twice with water
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-3e56019125d3448fb153a16b6fa7e368
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Linked notes

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