Acetyl chloride → 4-Acetamidophenethyl acetate

Reaction equation

[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][CH2:11][OH:12])=[CH:8][CH:7]=1.C(N(CC)CC)C.[O:22]1CCO[CH2:24][CH2:23]1>>[C:1]([O:12][CH2:11][CH2:10][C:9]1[CH:13]=[CH:14][C:6]([NH:5][C:23](=[O:22])[CH3:24])=[CH:7][CH:8]=1)(=[O:3])[CH3:2]

Participants

Reactant 4

HCID 6367Acetyl chloride

HCID 8471Triethylamine

HCID 312751,4-Dioxane2×

HCID 669044-Aminophenethyl alcohol

Product 1

HCID 125713974-Acetamidophenethyl acetate

Procedure

A solution of acetyl chloride (35.6 ml) in dioxan (110 ml) was added dropwise at 0° C. to a stirred mixture of p-aminophenethyl alcohol (34.3 g, Aldrich) and triethylamine (37.5 g) in dioxan (110 ml). When addition was complete, the mixture was stirred at room temperature for 17 hours, then poured into 2N aqu. HCl, saturated with NaCl, and extracted with ethyl acetate (×3). The combined extracts were washed with water and brine, dried over MgSO4 and evaporated in vacuo to give the desired product as a brown solid (55.3 g).