4-(Acetamidomethyl)benzoic acid → Methyl 4-(acetamidomethyl)benzoate

HRID 1282047Notes

Reaction equation

HRID 1282047 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)(=[O:3])[CH3:2].Cl.[CH3:16]O>>[C:1]([NH:4][CH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:16])=[O:11])=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 5060644-(Acetamidomethyl)benzoic acidHCID 21893726Hydrochloride methanol

Product 1

HCID 15550681Methyl 4-(acetamidomethyl)benzoate

Conditions

Temperature
40 °C

Procedure

4-Acetamidomethylbenzoic acid(4.0 g) was dissolved in 0.5% hydrochloric acid—methanol solution (100 ml). The mixture was stirred at 40° C. for 3.5 hr, and poured into ice water (300 ml) and extracted with ethyl acetate (100 ml×4). The extract was washed with saturated sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a pale-yellow solid (4.3 g). The obtained solid was crystallized from ethyl acetate (50 ml) to give the title compound (3.2 g) as pale-yellow white crystals, m.p.=110-111° C.

Workup

  1. extractionextracted with ethyl acetate (100 ml×4)
  2. washThe extract was washed with saturated sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-3565a980546b4174973b2d934a81f172
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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