Ethanol → 2,2,3',5'-Tetrachloro-4'-hydroxypropiophenone

HRID 1580528Notes

Reaction equation

HRID 1580528 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10](=[O:12])C)[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8].[CH:13]([Cl:16])(Cl)[Cl:14].ClCl.[CH2:19](O)C>>[Cl:14][C:13]([Cl:16])([CH3:19])[C:10]([C:4]1[CH:5]=[C:6]([Cl:9])[C:7]([OH:8])=[C:2]([Cl:1])[CH:3]=1)=[O:12]

Participants

5

Reactant 4

HCID 702EthanolHCID 6212ChloroformHCID 24526ChlorineHCID 869201-(3,5-Dichloro-4-hydroxyphenyl)ethanone

Product 1

HCID 215618932,2,3',5'-Tetrachloro-4'-hydroxypropiophenone

Procedure

A 500-milliliter reaction flask was charged with 21.9 grams (0.1 mole) of the 3',5'-dichloro-4'-hydroxyacetophenone, 250 grams of chloroform, and 10 grams of ethanol. The compound was chlorinated with 17.8 grams (0.25 mole) of chlorine gas added at 50°-55° C. over a period of 2.5 hours. The solution was evaporated under reduced pressure, and 27.1 grams of crude, white 2,2,3',5'-tetrachloro-4'-hydroxpropiophenone was obtained. Analysis calcd.: Hydrolyzable Cl, 24.6. Found: Hydrolyzable Cl, 22.3.

Workup

  1. customA 500-milliliter reaction flask
  2. additionadded at 50°-55° C. over a period of 2.5 hours
  3. customThe solution was evaporated under reduced pressure, and 27.1 grams of crude
  4. customwhite 2,2,3',5'-tetrachloro-4'-hydroxpropiophenone was obtained

Sources & evidence

ORD record
ord-ccb4a4d5a3934b14ad2383ea4d46aed0
Source dataset
uspto-grants-1976_01
Patent number
US03933472

Reaction notes

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