Hydrochloric Acid → N-[3-(4-Hydroxyphenyl)-1-methylpropyl]acetamide

HRID 1260501Notes

Reaction equation

HRID 1260501 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH:13]([NH:15][C:16](=[O:18])[CH3:17])[CH3:14])=[CH:7][CH:6]=1)(=O)C.C[O-].[Na+].Cl>CO>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][CH:13]([NH:15][C:16](=[O:18])[CH3:17])[CH3:14])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 670716934-(3-Acetylaminobutyl)phenyl acetate

Product 1

HCID 59956161N-[3-(4-Hydroxyphenyl)-1-methylpropyl]acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(3-Acetylaminobutyl)phenyl acetate (1.06 g, 4.25 mmol) was dissolved in 10 ml of methanol and, after addition of sodium methoxide (689.3 mg, 12.76 mmol), the reaction mixture was stirred at RT for 2 h. The pH was adjusted to 7 by adding dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic phases were combined and concentrated in vacuo. Yield: 805 mg (91%), M+H+: 208.15.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06112e365aa44e63ac3b8bca338ada48
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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