Dichloromethane → HCID 45272509, compound

HRID 1614887Notes

Reaction equation

HRID 1614887 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:26])[CH:23]([CH3:25])[CH3:24]>O>[CH: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:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 62325Isobutyryl chlorideHCID 811861,1,4,4-TetramethyltetralinHCID 6451240Aluminum(III) Chloride

Product 1

HCID 45272509HCID 45272509, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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, 1.00 mmol) were added anhydrous dichloromethane (1 mL), aluminum chloride (140 mg, 1.05 mmol), and isobutyryl chloride (112 mg, 1.05 mmol) followed by stirring at room temperature 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 (20/1) as an elution solvent. The yield was 97.4 mg (38%).

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-6176243e874449c1aced6cbc468c3be3
Source dataset
uspto-grants-2014_07
Patent number
US08765719B2

Reaction notes

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