Sulfuric Acid → 2-Chloro-1-[3,4-bis(acetyloxy)phenyl]ethanone

HRID 4114

Reaction equation

HRID 4114 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([OH:12])[CH:6]=1)=[O:4].S(=O)(=O)(O)O>C(OC(=O)C)(=O)C>[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:3](=[O:4])[CH3:2])=[C:7]([O:12][C:8](=[O:11])[CH3:7])[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 668342-Chloro-3',4'-dihydroxyacetophenone

Product 1

HCID 137646832-Chloro-1-[3,4-bis(acetyloxy)phenyl]ethanone

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of α-chloro-3',4'-dihydroxyacetophenone (9.33 g, 0.05 mole) in 78 ml of acetic anhydride was treated with 0.1 ml of concentrated sulfuric acid and stirred for 1.5 hours under an argon atmosphere. Initially, the reaction temperature rose to 40° C. and the starting material completely dissolved yielding a clear, colorless solution which was poured onto approximately 300 g of crushed ice. After standing for one hour, the crystallized product was filtered, washed with cold water (200 ml) and dried in vacuo overnight at room temperature; yield: 11.5 g.

Workup

  1. customrose to 40° C.
  2. dissolutionthe starting material completely dissolved
  3. customyielding a clear, colorless solution which
  4. waitAfter standing for one hour
  5. filtrationthe crystallized product was filtered
  6. washwashed with cold water (200 ml)
  7. customdried in vacuo overnight at room temperature

Sources & evidence

ORD record
ord-c98143d1d5664d11907a5d25e56ab78d
Source dataset
uspto-grants-1988_02
Patent number
US04723002

Linked notes

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