Methanol → Methyl 2-ethoxybenzoate

HRID 618805Notes

Reaction equation

HRID 618805 reaction equation
S(=O)(=O)(O)O.[CH2:6]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])[CH3:7].[CH3:18]O>ClCCl>[CH2:6]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([O:13][CH3:18])=[O:12])[CH3:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 672522-Ethoxybenzoic acid

Product 1

HCID 347794Methyl 2-ethoxybenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Concentrated sulphuric acid (0.5 ml) was added to a solution of 2-ethoxybenzoic acid (50 g, 0.301 mol) in methanol (500 ml) and the resulting mixture heated under reflux for 70 hours, then evaporated under reduced pressure to give an oil which was dissolved in dichloromethane (300 ml). This solution was washed successively with water (150 ml), aqueous sodium bicarbonate solution (150 ml) and water (150 ml), then evaporated under reduced pressure to give the title compound (49.7 g) as an oil. δ (CDCl3): 1.44 (3H,t), 3.90 (3H,s), 4.12 (2H,q), 6.95 (2H,m), 7.44 (1H,t), 7.78 (1H,d).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 70 hours
  3. customevaporated under reduced pressure
  4. customto give an oil which
  5. washThis solution was washed successively with water (150 ml), aqueous sodium bicarbonate solution (150 ml) and water (150 ml)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e7be91ba62c44fffa069b89ee1c926b3
Source dataset
uspto-grants-1999_09
Patent number
US05955611

Reaction notes

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