Sulfuric Acid → 2-Phenyl-5-methoxy-6,7-dichloro-1-indanone

HRID 1156198Notes

Reaction equation

HRID 1156198 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:18])[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH2:11])[CH:5]=[CH:4][C:3]=1[O:19][CH3:20].S(=O)(=O)(O)O>C(Cl)Cl>[C:12]1([CH:10]2[CH2:11][C:5]3[C:6](=[C:7]([Cl:8])[C:2]([Cl:1])=[C:3]([O:19][CH3:20])[CH:4]=3)[C:9]2=[O:18])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 109248102,3-Dichloro-4-(2-phenylacryloyl)anisole

Product 1

HCID 109904442-Phenyl-5-methoxy-6,7-dichloro-1-indanoneYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,3-Dichloro-4-(2-phenylacryloyl)anisole (8.2 g., 26.8 mmol) in 215 ml. of methylene chloride is added dropwise over a 4.5 hr. period to a stirred solution of 107 ml. of sulfuric acid in 107 ml. of methylene chloride at 0°-5° under an atmosphere of argon. Following addition, the reaction mixture is stirred for 0.5 hr., poured over about 300 g. of crushed ice and the aqueous-organic phases separated. The aqueous phase is extracted with methylene chloride and the combine methylene chloride solutions sequentially washed with water and then dried over magnesium sulfate. Removal of the solvent affords 8.52 g. of solid which crystallized from benzene-cyclohexane provides 4.59 g. (56% yield) of 2-phenyl-5-methoxy-6,7-dichloro-1-indanone, m.p. 193.5°-196.5°.

Workup

  1. customat 0°-5°
  2. additionaddition
  3. addition, poured over about 300 g
  4. customof crushed ice and the aqueous-organic phases separated
  5. extractionThe aqueous phase is extracted with methylene chloride
  6. washthe combine methylene chloride solutions sequentially washed with water
  7. dry with materialdried over magnesium sulfate
  8. customRemoval of the solvent
  9. customaffords 8.52 g
  10. customof solid which crystallized from benzene-cyclohexane
  11. customprovides 4.59 g

Sources & evidence

ORD record
ord-56d92672053a4e29b5159e72c1ce07d2
Source dataset
uspto-grants-1982_06
Patent number
US04334088

Reaction notes

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