Sodium Chloride → Acetophenone

HRID 405009Notes

Reaction equation

HRID 405009 reaction equation
CC1(C)N([O])C(C)(C)CCC1.[Na+].[Cl-].[C:14]1([CH:20]([OH:22])[CH3:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCCl>[C:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 74091-PhenylethanolHCID 2724126Tempo

Product 1

HCID 7410Acetophenone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Fe(NO3)3.9H2O (16.1607 g, 40.0 mmol), TEMPO (6.2510 g, 40.0 mmol), NaCl (2.3377 g, 40.0 mmol) and DCE (400 mL) were added to a 2 L-three-necked flask, and were stirred for 10 mins at room temperature under oxygen atmosphere. 1-Phenyl ethanol (488.64 g, 4.0 mol) was then added dropwise to the reaction solution. The reaction was exothermic, and the reaction temperature was kept below 50° C. The reaction was monitored by TLC till it was complete. The reaction solvent DCE was recovered after distillation under atmospheric pressure (350 mL, recovery of 88%) and acetophenone was obtained after further distillation under reduced pressure (b.p. 98˜100° C./20 mmHg, 436.6414 g, 91%).

Workup

  1. customwas kept below 50° C
  2. customThe reaction solvent DCE was recovered
  3. distillationafter distillation under atmospheric pressure (350 mL, recovery of 88%)

Sources & evidence

ORD record
ord-9950e3bfc44c490b9fbd31a5201ccc21
Source dataset
uspto-grants-2014_06
Patent number
US08748669B2

Reaction notes

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