Benzoic Acid → Methyl Benzoate

HRID 1644691Notes

Reaction equation

HRID 1644691 reaction equation
S(=O)(=O)(O)O.[C:6]([OH:14])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:15]O>>[CH3:15][O:13][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 243Benzoic AcidHCID 887MethanolHCID 1118Sulfuric Acid

Product 1

HCID 7150Methyl Benzoate

Procedure

Concentrated sulfuric acid (3.4 mL) was added drop-wise to an ice cold mixture of 3-methanesulfanyl benzoic acid (5.0 g, 30 mmol) and methanol (30 mL). After the addition was complete, the reaction mixture was warmed to room temperature, then stirred overnight. The reaction mixture was concentrated in vacuo. The resulting oil was diluted with ethyl acetate, and then washed with water followed by saturated sodium bicarbonate. The organic phase was dried over MgSO4, filtered, and concentrated to give 5.4 g of 3-methanesulfanyl benzoic acid methyl ester as a clear oil. This crude product was used in subsequent steps without further purification.

Workup

  1. additionAfter the addition
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionThe resulting oil was diluted with ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f22ba74f37a849a6a9a9ca060ccbbb63
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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