Acetyl chloride → 4-Acetamidophenethyl acetate

HRID 483370Notes

Reaction equation

HRID 483370 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

5

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 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).

Workup

  1. additionWhen addition
  2. additionpoured into 2N aqu
  3. extractionHCl, saturated with NaCl, and extracted with ethyl acetate (×3)
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-1dd63b07939245f2bdd0bdee7414e310
Source dataset
uspto-grants-1993_07
Patent number
US05225431

Reaction notes

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