Benzene → HCID 12317491, compound

HRID 918104Notes

Reaction equation

HRID 918104 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[C:10](=[O:11])[CH2:9][CH2:8][CH2:7]1)=[O:5].[C:12]1([C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)O)[OH:13].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[C:10]12([O:13][C:12]3[CH:14]=[CH:16][CH:17]=[CH:18][C:19]=3[O:11]1)[CH2:9][CH2:8][CH2:7][CH:6]2[C:4]([O:3][CH2:2][CH3:1])=[O:5]

Participants

6

Reactant 4

HCID 241BenzeneHCID 289CatecholHCID 6101p-Toluenesulfonic acidHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 12317491HCID 12317491, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 15.7 g. of ethyl cyclopentanone-2-carboxylate, 11 g. of pyrocatechol, 0.5 g. of p-toluenesulphochloride and 0.5g. of p-toluenesulphonic acid in 100 cc. of anhydrous benzene is refluxed until the theoretical amount of water no longer distils azeotropically. The mixture is washed first with dilute NaOH and then with H2O until neutral. After drying with Na2SO4 the solvent is removed under vacuum. The residual oil is fractionated, and the desired product boils at 136°-139°C./0.3 mm.

Workup

  1. additionA mixture of 15.7 g
  2. customno longer distils azeotropically
  3. washThe mixture is washed first with dilute NaOH
  4. dry with materialAfter drying with Na2SO4 the solvent
  5. customis removed under vacuum

Sources & evidence

ORD record
ord-7126e853b86140bcbd2b4e865e4ed389
Source dataset
uspto-grants-1976_07
Patent number
US03969368

Reaction notes

Loading…