Dichloromethane → HCID 22226103, compound

HRID 1744911Notes

Reaction equation

HRID 1744911 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([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)[CH2:6][CH3:7].[Cl-].[Cl-].[Cl-].[Al+3].Cl[CH2:28]Cl>>[CH2:5]([O:8][C:9]1[C:10]([C:1](=[O:3])[CH2:2][CH3:28])=[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)[CH2:6][CH3:7]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 222261103-n-Propoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene2×

Product 1

HCID 22226103HCID 22226103, compound

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (0.831 g, 11.7 mmol) was added to a stirring solution of 3-n-propoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (Intermediate 6, 2.4 g, 9.7 mmol) in dichloromethane (100 mL), and the solution was cooled to 0° C. Aluminum trichloride (1.56 g, 11.7 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-9b119ade55ee4eddb885dd59d670fbab
Source dataset
uspto-grants-2006_03
Patent number
US07019034B2

Reaction notes

Loading…