Hydrochloric Acid → Acetophenone

HRID 1420778Notes

Reaction equation

HRID 1420778 reaction equation
N[C:2]1[C:3](O)=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].C1(CCCCOC2C=CC(C(Cl)=O)=CC=2)C=CC=CC=1.Cl>CC(C)=O>[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 4592943-Amino-2-hydroxyacetophenoneHCID 11055348Benzoyl chloride, 4-(4-phenylbutoxy)-

Product 1

HCID 7410Acetophenone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

3'-Amino-2'-hydroxyacetophenone (1.51 g, 10 mmol) was dissolved in 50 ml of acetone, and potassium carbonate (6.90 g, 50 mmol) was added to the solution. 4-(4-Phenylbutoxy)benzoyl chloride (2.89 g, 10 mmol) was added dropwise to the mixture under stirring at 0° C., and stirring was conducted further for 3 hours. The resultant reaction mixture was poured into a 10% hydrochloric acid (100 ml) to conduct extraction with chloroform. An organic layer was washed with water, dried and then concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel. Crystals obtained from a fraction eluted with chloroform were recrystallized from ethanol to obtain 2.82 g (yield: 70%) of 2-hydroxy-3-[4-(4-phenylbutoxy)benzamido)]acetophenone.

Workup

  1. stirringstirring
  2. customThe resultant reaction mixture
  3. extractionextraction with chloroform
  4. washAn organic layer was washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customCrystals obtained from a fraction
  8. washeluted with chloroform
  9. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-fa7da0d242054ce3b143f442c885a3b1
Source dataset
uspto-grants-2000_06
Patent number
US06071943

Reaction notes

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