Dichloromethane → HCID 45273384, compound

HRID 1614885Notes

Reaction equation

HRID 1614885 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6][C:5]([CH3:15])([CH3:14])[C:4]=2[CH:3]=1.ClCCl.[Cl-].[Al+3].[Cl-].[Cl-].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[C:24]1([C:23]([C:11]2[C:2]([OH:1])=[CH:3][C:4]3[C:5]([CH3:15])([CH3:14])[CH2:6][CH2:7][C:8]([CH3:13])([CH3:12])[C:9]=3[CH:10]=2)=[O:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 2687865,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-olHCID 6451240Aluminum(III) Chloride

Product 1

HCID 45273384HCID 45273384, 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-2-hydroxy-5,5,8,8-tetramethylnaphthalene (204 mg, 1.00 mmol) were added anhydrous dichloromethane (1 mL), aluminum chloride (148 mg, 1.12 mmol), and benzoyl chloride (155 mg, 1.10 mmol) followed by stirring at 60° C. for 1 hour. 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 27.3 mg (9%).

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-3e72399696424f17bb8bf6349d4ac7d9
Source dataset
uspto-grants-2014_07
Patent number
US08765719B2

Reaction notes

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