Methanol → HCID 13362534, compound

HRID 1979555Notes

Reaction equation

HRID 1979555 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([C:6]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])=[O:5].S(=O)(=O)(O)O.[CH3:25]O>>[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([C:6]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:7]=1[C:8]([O:10][CH3:25])=[O:9])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 13533630HCID 13533630, compound

Product 1

HCID 13362534HCID 13362534, compound

Procedure

A solution of 2.0 g (7.19 mmoles) of [2-(2-fluorobenzoyl)-4-chlorobenzoic acid], in 40 ml of methanol and 0.3 ml of sulfuric acid was refluxed for 10 hrs and then evaporated. The residue was partitioned between 50 ml of dichloromethane and 30 ml of dilute ammonium hydroxide, and the organic layer was dried and evaporated. The resulting oil was dissolved in 20 ml of dichloromethane, filtered through 25 g of Florisil and eluted with dichloromethane. The solvent was evaporated and the oil was crystallized from ether and recrystallized from dichloromethane/ether/petrol to give white rods: mp 115°-116° C.

Workup

  1. customevaporated
  2. customThe residue was partitioned between 50 ml of dichloromethane and 30 ml of dilute ammonium hydroxide
  3. customthe organic layer was dried
  4. customevaporated
  5. dissolutionThe resulting oil was dissolved in 20 ml of dichloromethane
  6. filtrationfiltered through 25 g of Florisil
  7. washeluted with dichloromethane
  8. customThe solvent was evaporated
  9. customthe oil was crystallized from ether
  10. customrecrystallized from dichloromethane/ether/petrol
  11. customto give white rods

Sources & evidence

ORD record
ord-71b6348fdfee4f999f29513d1ecec252
Source dataset
uspto-grants-1984_11
Patent number
US04481142

Reaction notes

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