Methanol → Methyl 4-(1-acetamido-1-methylethyl)benzoate

HRID 1282160Notes

Reaction equation

HRID 1282160 reaction equation
[C:1]([NH:4][C:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)([CH3:7])[CH3:6])(=[O:3])[CH3:2].S(=O)(=O)(O)O.[CH3:22]O>>[C:1]([NH:4][C:5]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([O:14][CH3:22])=[O:13])=[CH:15][CH:16]=1)([CH3:7])[CH3:6])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 184231434-(2-Acetamidopropan-2-yl)benzoic acid

Product 1

HCID 18423021Methyl 4-(1-acetamido-1-methylethyl)benzoate

Procedure

A suspension of 4-(1-acetamido-1-methylethyl)benzoic acid (73.4 g) and sulfuric acid (0.7 ml) in methanol (370 ml) was refluxed for 16 hr. The solvent was evaporated and 10% aqueous sodium hydrogencarbonate (500 ml) was added and the mixture was extracted with ethyl acetate (500 ml). The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was recrystallized from ethyl acetate-isopropyl ether to give the title compound (39.0 g) as pale-yellow crystals, m.p.=165-167° C.

Workup

  1. temperaturewas refluxed for 16 hr
  2. customThe solvent was evaporated
  3. addition10% aqueous sodium hydrogencarbonate (500 ml) was added
  4. extractionthe mixture was extracted with ethyl acetate (500 ml)
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe obtained residue was recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-db51aea23c3d45ca8145e96ab3e8e4c2
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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