Propionyl chloride → HCID 22226102, compound

HRID 1744906Notes

Reaction equation

HRID 1744906 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[CH2:6]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]([CH3:22])([CH3:21])[CH2:14][CH2:15][C:16]([CH3:20])([CH3:19])[C:17]=2[CH:18]=1)[CH3:7].[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[CH2:6]([O:8][C:9]1[C:10]([C:1](=[O:4])[CH2:2][CH3:3])=[CH:11][C:12]2[C:13]([CH3:21])([CH3:22])[CH2:14][CH2:15][C:16]([CH3:20])([CH3:19])[C:17]=2[CH:18]=1)[CH3:7]

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 2267056-Ethoxy-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 22226102HCID 22226102, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Propionyl chloride (1.44 mL, 16.6 mmol) was added to a stirring solution of 3-ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (Intermediate 2, 3.5 g, 15.1 mmol) in dichloromethane (100 mL), and the solution was cooled to 0° C. Aluminum trichloride (2.21 g, 16.6 mmol) was added over two to three minutes, the ice-bath was removed, the yellow solution was stirred for 1 h at room temperature. The solution was poured over ice in a separatory funnel, and the products were extracted three times with ether. The combined organic layers were washed with 10% aqueous sodium hydroxide, brine and dried over magnesium sulfate. The solvent was removed in vacuo to give the title compound as a solid.

Workup

  1. customthe ice-bath was removed
  2. additionThe solution was poured over ice in a separatory funnel
  3. extractionthe products were extracted three times with ether
  4. washThe combined organic layers were washed with 10% aqueous sodium hydroxide, brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-70db157907e0418d8ef64e5f8bf885ff
Source dataset
uspto-grants-2006_03
Patent number
US07019034B2

Reaction notes

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