Water → N-(1-(4-hydroxymethylphenyl)-1-methylethyl)acetamide

HRID 1282161Notes

Reaction equation

HRID 1282161 reaction equation
[C:1]([NH:4][C:5]([C:8]1[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[CH:10][CH:9]=1)([CH3:7])[CH3:6])(=[O:3])[CH3:2].[BH4-].[Li+].O>O1CCCC1>[OH:13][CH2:12][C:11]1[CH:10]=[CH:9][C:8]([C:5]([NH:4][C:1](=[O:3])[CH3:2])([CH3:7])[CH3:6])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 18423021Methyl 4-(1-acetamido-1-methylethyl)benzoate

Product 1

HCID 18423112N-(1-(4-hydroxymethylphenyl)-1-methylethyl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(1-acetamido-1-methylethyl)benzoate (37.14g) in tetrahydrofuran (370 ml) was added lithium borohydride (6.88 g) and the mixture was refluxed for 19 hr. The reaction mixture was poured into water (1000 ml) and extracted with ethyl acetate (1000 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 to give the title compound (18.24 m.p.=126-129° C.

Workup

  1. temperaturethe mixture was refluxed for 19 hr
  2. extractionextracted with ethyl acetate (1000 ml)
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-eca1881ab8af41a0a27c81f76b283411
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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