Acetyl chloride → N-[5-(Hydroxymethyl)-2-methylphenyl]acetamide

HRID 1176222Notes

Reaction equation

HRID 1176222 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[CH:6][C:7]=1[CH3:8].C(N(CC)CC)C.[C:18](Cl)(=[O:20])[CH3:19]>C(Cl)(Cl)Cl>[OH:10][CH2:9][C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([NH:1][C:18](=[O:20])[CH3:19])[CH:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 586243(3-Amino-4-methylphenyl)methanol

Product 1

HCID 14543056N-[5-(Hydroxymethyl)-2-methylphenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The solution of 11.3 g of (3-amino-4-methylphenyl)methanol in 500 ml of chloroform is cooled to 0° C. with stirring and admixed with 13.4 ml of triethylamine. 6.03 ml of acetyl chloride are slowly added dropwise. Subsequently, the mixture is stirred at 0° C. over 2 hours. The reaction mixture is poured onto water (1 l) and extracted with dichloromethane (2×350 ml). The organic phases are washed with brine (350 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a slightly brownish solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.10 (1:2 dichloromethane-diethyl ether); Rt=2.14.

Workup

  1. stirringSubsequently, the mixture is stirred at 0° C. over 2 hours
  2. additionThe reaction mixture is poured onto water (1 l)
  3. extractionextracted with dichloromethane (2×350 ml)
  4. washThe organic phases are washed with brine (350 ml)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-f7f38442dde74c23ac1e995926e9729f
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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