Water → 5-Chloro-6-cyclohexyl-1-benzofuran-2(3H)-one

HRID 1414050Notes

Reaction equation

HRID 1414050 reaction equation
[Cl:1][C:2]1[C:3]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][C:5]([OH:12])=[C:6]([CH2:8][C:9](O)=[O:10])[CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][C:5]2[O:12][C:9](=[O:10])[CH2:8][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 20158185HCID 20158185, compound

Product 1

HCID 688065-Chloro-6-cyclohexyl-1-benzofuran-2(3H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5 g of 5-chloro-4-cyclohexyl-2-hydroxyphenylacetic acid are dissolved in toluene with heating, 50 mg of p-toluenesulphonic acid are added, and the mixture is boiled in a water separator for 3 hours. The oil obtained after evaporation is purified on a 100-fold quantity of silica gel Merck. The desired product is eluted with chloroform and recrystallized from methylene chloride/petroleum ether. The crystals have an M.P. of 100°-102°.

Workup

  1. temperaturewith heating
  2. customThe oil obtained
  3. customafter evaporation
  4. customis purified on a 100-fold quantity of silica gel Merck
  5. washThe desired product is eluted with chloroform
  6. customrecrystallized from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-c9d065ab99f54f669bac81ae479ce5b0
Source dataset
uspto-grants-1981_02
Patent number
US04252817

Reaction notes

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