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

HRID 1287516Notes

Reaction equation

HRID 1287516 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:11](=[O:20])[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH2:13].S(=O)(=O)(O)O>ClCCl>[C:14]1([CH:12]2[CH2:13][C:4]3[C:3](=[C:2]([Cl:1])[C:7]([Cl:8])=[C:6]([O:9][CH3:10])[CH:5]=3)[C:11]2=[O:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2',3' -Dichloro-4'-methoxy-2-phenylacrylophenone (160 g.) dissolved in dichloromethane (4 liters) is added dropwise to a mixture of 12N sulfuric acid (2 liters) and dichloromethane (2 liters) at <5°C. over a 3-hour period. The reaction mixture is stirred for an additional 30 minutes then poured slowly onto crushed ice. The dichloromethane layer is separated, washed with saturated sodium chloride solution, then dried over anhydrous magnesium sulfate. The solvent is removed under reduced pressure leaving a light tan solid residue. On drying in a steam oven at 70°C., 120.5 g. of product (75%) is obtained, mp 187°-192°C. A sample recrystallized from benzene-cyclohexane (2:1) melts at 193°-195°C.

Workup

  1. additionthen poured slowly
  2. customonto crushed ice
  3. customThe dichloromethane layer is separated
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent is removed under reduced pressure
  7. customleaving a light tan solid residue
  8. customOn drying in a steam oven at 70°C.

Sources & evidence

ORD record
ord-9cc24fdc17024a12958618f0f8c21d33
Source dataset
uspto-grants-1976_10
Patent number
US03984552

Reaction notes

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