Ethylene → 6-Ethoxy-2-tetralone

HRID 1385893

Reaction equation

HRID 1385893 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](Cl)=[O:12])=[CH:6][CH:5]=1)[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:18]=[CH2:19]>ClCCl>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]2[C:7](=[CH:6][CH:5]=1)[CH2:10][C:11](=[O:12])[CH2:19][CH2:18]2)[CH3:2]

Participants

5

Reactant 3

HCID 6325EthyleneHCID 6451240Aluminum(III) ChlorideHCID 116297822-(4-ethoxyphenyl)acetyl Chloride

Product 1

HCID 46940316-Ethoxy-2-tetralone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

39.1 g (0.20 mol) of 4-ethoxyphenylacetyl chloride in 200 ml of dichloromethane were added dropwise in the course of 1 hour at −78° C. to 53.4 g (0.4 mol) of aluminum chloride in 800 ml of dichloromethane. A vigorous stream of ethylene was subsequently passed in in the course of 15 minutes, and the mixture was allowed to come to room temperature and stirred for a further 3 hours. The dark red solution was cooled to 0° C. and carefully treated with 300 ml of ice-water. After phase separation, the organic phase was washed with 2N HCl (3×) and saturated sodium hydrogen carbonate solution, dried and evaporated on a rotary evaporator. After purification by column chromatography with petroleum ether/ethyl acetate (9:1, 8:2), 20.9 g (56% of theory) of a yellow syrup were obtained.

Workup

  1. customwas subsequently passed in in the course of 15 minutes
  2. customto come to room temperature
  3. customAfter phase separation
  4. washthe organic phase was washed with 2N HCl (3×) and saturated sodium hydrogen carbonate solution
  5. customdried
  6. customevaporated on a rotary evaporator
  7. customAfter purification by column chromatography with petroleum ether/ethyl acetate (9:1, 8:2), 20.9 g (56% of theory) of a yellow syrup
  8. customwere obtained

Sources & evidence

ORD record
ord-0fe0cdefbb12467cbe006d2f5dd21b98
Source dataset
uspto-grants-2001_07
Patent number
US06265398B1

Linked notes

Loading…