Acetyl chloride → 2-Acetylamino-4-chlorophenol

HRID 1763558Notes

Reaction equation

HRID 1763558 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18].Cl.C(N(CC)CC)C>O1CCCC1>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([OH:9])=[C:2]([NH:1][C:17](=[O:19])[CH3:18])[CH:7]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 72652-Amino-4-chlorophenolHCID 8471TriethylamineHCID 11130Triethylamine hydrochloride

Product 1

HCID 952582-Acetylamino-4-chlorophenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 100 grams of 2 amino-4-chlorophenol (0.70 mole) in 1 liter of tetrahydrofuran is added 71 grams of triethylamine (0.70 mole). The resulting solution is cooled with an ice bath. To the solution is then slowly added 55 grams of acetyl chloride (0.70 mole) in 200 ml. of tetrahydrofuran. A precipitate forms (triethylamine hydrochloride). The solution is then filtered and the filtrate evaporated under reduced pressure, yielding a dark solid residue. Recrystallization of the residue from methylene chloride and petroleum ether (1:1) yields 4-chloro-2-acetamidophenol.

Workup

  1. temperatureThe resulting solution is cooled with an ice bath
  2. filtrationThe solution is then filtered
  3. customthe filtrate evaporated under reduced pressure
  4. customyielding a dark solid residue
  5. customRecrystallization of the residue from methylene chloride and petroleum ether (1:1)

Sources & evidence

ORD record
ord-520374ee63f54a6db1c3ba45691e959b
Source dataset
uspto-grants-1978_09
Patent number
US04112117

Reaction notes

Loading…