Thionyl Chloride → Isoxepac

HRID 971601

Reaction equation

HRID 971601 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][C:10]=1[C:19]([OH:21])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O>>[O:21]=[C:19]1[C:7]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[CH2:1][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][C:10]1=2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 203861514-Benzyloxy-3-carboxyphenylacetic acid

Product 1

HCID 41448Isoxepac

Procedure

A sample of 4-benzyloxy-3-carboxyphenylacetic acid is treated with an excess of thionyl chloride at reflux for 2 hours. The excess thionyl chloride is removed in vacuo and the remaining 4-benzyloxy-3-(chlorocarbonyl)phenylacetyl chloride is dissolved in methylene chloride-nitromethane and treated with an equivalent amount of aluminum chloride. The reaction mixture is stirred several hours at room temperature, refluxed for two hours and quenched with dilute hydrochloric acid. The layers are separated, the organic phase dried and evaporated in vacuo to a residue which, on crystallization from isopropyl alcohol yields 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid, mp 137°-138° C.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe excess thionyl chloride is removed in vacuo
  3. dissolutionthe remaining 4-benzyloxy-3-(chlorocarbonyl)phenylacetyl chloride is dissolved in methylene chloride-nitromethane
  4. additiontreated with an equivalent amount of aluminum chloride
  5. temperaturerefluxed for two hours
  6. customquenched with dilute hydrochloric acid
  7. customThe layers are separated
  8. customthe organic phase dried
  9. customevaporated in vacuo to a residue which, on crystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-d2464932df664dc9bb9610d0a88f01f3
Source dataset
uspto-grants-1979_07
Patent number
US04160781

Linked notes

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