p-Toluenesulfonic acid → HCID 19741682, compound

HRID 2255201Notes

Reaction equation

HRID 2255201 reaction equation
[CH2:1]([C:4]1[C:5]([OH:13])=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)[CH:2]=[CH2:3].[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](Cl)=O.[OH-].[K+].C1(C)C=CC(S(O)(=O)=O)=CC=1>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1C=CC=CC=1>[CH2:1]([C:4]1[C:5]2[O:13][C:17]([C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[F:14])=[CH:11][C:10](=[O:12])[C:6]=2[CH:7]=[CH:8][CH:9]=1)[CH:2]=[CH2:3]

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 98082-Fluorobenzoyl chlorideHCID 14797Potassium HydroxideHCID 130269161-(3-Allyl-2-hydroxyphenyl)ethanone

Product 1

HCID 19741682HCID 19741682, compoundYield 58.3%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 0.528 g (3 mmol) of 3'-allyl-2'-hydroxyacetophenone, 0.57 g (3.6 mmol) of 2-fluorobenzoyl chloride, 0.509 g (1.5 mmol) of tetra-n-butylammonium bisulfate, 20 ml of 10% aqueous potassium hydroxide and 20 ml of benzene was heated at 80° C. for 3 hours. The layers were separated and the benzene layer washed thoroughly with water (3×20 ml) and the water removed from the benzene layer by azeotropic distillation. The resulting residue was treated with 1.7 g (9 mmol) of p-toluenesulphonic acid and benzene (25 ml) and heated for two hours with azeotropic removal of water. The benzene solution was washed with 8% aqueous sodium bicarbonate (50 ml) and the solvent evaporated in vacuo. The resulting residue was recrystallized from ethyl acetate to give 0.49 g (58%) of 8-allyl-2-(2-fluorophenyl)-4H-benzopyran-4-one as white solid: M.P. 78°-81° C.; TLC R f 0.40 in 10:1 hexane-ethylacetate.

Workup

  1. customThe layers were separated
  2. washthe benzene layer washed thoroughly with water (3×20 ml)
  3. customthe water removed from the benzene layer by azeotropic distillation
  4. washThe benzene solution was washed with 8% aqueous sodium bicarbonate (50 ml)
  5. customthe solvent evaporated in vacuo
  6. customThe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0911b4c2802a4a6bb9ef5ee8127b87ef
Source dataset
uspto-grants-1993_08
Patent number
US05238954

Reaction notes

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