Methanol → HCID 19036388, compound

HRID 264546Notes

Reaction equation

HRID 264546 reaction equation
[CH2:1]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([Cl:15])[CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:16])[CH:2]=CC.C[OH:18]>ClCCl>[Cl:15][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[C:6](=[O:16])[CH:5]([CH2:1][CH:2]=[O:18])[CH2:14][CH2:13]2

Participants

4

Reactant 2

HCID 887MethanolHCID 543159702-(2-Buten-1-yl)-8-chloro-1-tetralone

Product 1

HCID 19036388HCID 19036388, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.7 g of 2-(2-buten-1-yl)-8-chloro-1-tetralone were dissolved in a mixture of 220 ml of dichloromethane and 60 ml of methanol, cooled to -75° and the double bond was ozonized in the usual manner. After flushing the reaction mixture with oxygen and argon, 4.8 ml of dimethyl sulfide were added dropwise. The mixture was left to warm slowly to room temperature and was stirred for an additional 15 hours. The crude product (10.8 g) was dissolved in about 100 ml of dichloromethane and added to a mixture of 12 ml of 10% aqueous oxalic acid, 120 g of silica gel and 300 ml of dichloromethane. The mixture was stirred at room temperature for 2 hours. 6.4 g (83%) of 8-chloro-2-(2-oxoethyl)-1-tetralone were obtained as a pale brown oil by extraction with dichloromethane.

Workup

  1. temperaturecooled to -75°
  2. customAfter flushing the reaction mixture with oxygen and argon, 4.8 ml of dimethyl sulfide
  3. additionwere added dropwise
  4. waitThe mixture was left
  5. dissolutionThe crude product (10.8 g) was dissolved in about 100 ml of dichloromethane
  6. additionadded to a mixture of 12 ml of 10% aqueous oxalic acid, 120 g of silica gel and 300 ml of dichloromethane
  7. stirringThe mixture was stirred at room temperature for 2 hours

Sources & evidence

ORD record
ord-4fb7c5fdc98843538413e4f5efd9223a
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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