Dichloromethane → HCID 45271609, compound

HRID 1614886Notes

Reaction equation

HRID 1614886 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.ClCCl.[Cl-].[Al+3].[Cl-].[Cl-].[C:22](Cl)(=[O:25])[CH2:23][CH3:24]>O>[CH2:23]([C:22]([C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:14])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=2[CH:7]=1)=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 62324Propionyl chlorideHCID 811861,1,4,4-TetramethyltetralinHCID 6451240Aluminum(III) Chloride

Product 1

HCID 45271609HCID 45271609, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The synthesis process is as set forth in the chemical reaction formula below. To 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene (188 mg, 1 mmol) were added anhydrous dichloromethane (1 mL), aluminum chloride (148 mg, 1.12 mmol), and propionyl chloride (101 mg, 1.10 mmol) followed by stirring at 60° C. for 3 hours. The reaction solution was poured into cold water and extracted by ethyl acetate. The organic layer was washed by water, a saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography using hexane/ethyl acetate (30/1) as an elution solvent. The yield was 66.4 mg (27%).

Workup

  1. extractionextracted by ethyl acetate
  2. washThe organic layer was washed by water
  3. dry with materiala saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5b8185199c914f62af48d0b90d825276
Source dataset
uspto-grants-2014_07
Patent number
US08765719B2

Reaction notes

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