Water → 2-Chloro-1,2-bis(4-methoxyphenyl)ethan-1-one

HRID 2059204Notes

Reaction equation

HRID 2059204 reaction equation
[C:1]1([C:9]([CH:11]([C:13]2[CH:20]=[CH:19][C:16]([O:17][CH3:18])=[CH:15][CH:14]=2)O)=[O:10])[CH:8]=[CH:7][C:4]([O:5][CH3:6])=[CH:3][CH:2]=1.N1C=CC=CC=1.S(Cl)([Cl:29])=O.O>CCOCC>[CH3:6][O:5][C:4]1[CH:7]=[CH:8][C:1]([C:9]([CH:11]([Cl:29])[C:13]2[CH:20]=[CH:19][C:16]([O:17][CH3:18])=[CH:15][CH:14]=2)=[O:10])=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 954154,4'-Dimethoxybenzoin2×

Product 1

HCID 38625232-Chloro-1,2-bis(4-methoxyphenyl)ethan-1-oneYield 36%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

One hundred grams (0.37 mole) of anisoin and 45 ml (0.55 mole) of pyridine were placed in a beaker and heated until the anisoin was completely in solution. After cooling the beaker in an ice bath, a solid was formed. This solid was broken up and then 36 ml (0.50 mole) of thionyl chloride was added with stirring, forming a liquid mixture. After 1 hr, 250 ml water was added and the organic materials extracted with ether, washed with water, dried over Na2SO4 and evaporated to afford a crude oil. Most of the oil was taken up in ether and a residual solid was filtered away. Cooling resulted in a yellow-brown solid which was filtered and collected. Recrystallization again from ether yielded 37.9 g (36%) of a solid. The product had a melting point of about 80°-81° C.

Workup

  1. temperatureAfter cooling the beaker in an ice bath
  2. customa solid was formed
  3. customforming a liquid mixture
  4. extractionthe organic materials extracted with ether
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customto afford a crude oil
  9. filtrationa residual solid was filtered away
  10. temperatureCooling
  11. customresulted in a yellow-brown solid which
  12. filtrationwas filtered
  13. customcollected
  14. customRecrystallization again from ether

Sources & evidence

ORD record
ord-d1380386cf00409daac9b0626d8ec877
Source dataset
uspto-grants-1982_03
Patent number
US04322428

Reaction notes

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