Reaction #927225

ord-05de96853e1a494aa9244e74f4bac646

Reaction equation

O
water
CCN(CC)CC
triethylamine
CC(=O)Nc1ccc(O)cc1
para-acetylaminophenol
CCCCCCCCCCCC(=O)Cl
lauroyl chloride
→
CCCCCCCCCCCC(=O)c1cc(NC(C)=O)ccc1O
Lauroyl [4-(N-acetylamino)]phenol
Yield 12.0%

Reactants

O
water
CCN(CC)CC
triethylamine
CC(=O)Nc1ccc(O)cc1
para-acetylaminophenol
CCCCCCCCCCCC(=O)Cl
lauroyl chloride

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe product precipitates
  2. 2
    WashIt is washed with heptane
  3. 3
    Otherdried under vacuum

Procedure

An equivalent amount in moles of para-acetylaminophenol and lauroyl chloride are placed in contact at 0° C. in DMF (dilution=15%) in the presence of one molar equivalent of triethylamine. The mixture is allowed to warm to room temperature with stirring and the reaction medium is then poured into water and the product precipitates. It is washed with heptane and then dried under vacuum. The yield is 12%. The elemental analysis is in accordance with the structure.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06365135B1uspto-grants-2002_04