Water → Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-

HRID 650577

Reaction equation

HRID 650577 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][C:6]1([CH3:19])[C:15]2[C:10](=[CH:11][C:12]([CH3:16])=[CH:13][CH:14]=2)[C:9]([CH3:18])([CH3:17])[CH2:8][CH2:7]1.[C:20](Cl)(=[O:22])[CH3:21].O>C(Cl)Cl>[CH3:16][C:12]1[C:13]([C:20](=[O:22])[CH3:21])=[CH:14][C:15]2[C:6]([CH3:19])([CH3:5])[CH2:7][CH2:8][C:9]([CH3:18])([CH3:17])[C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 811871,2,3,4-Tetrahydro-1,1,4,4,6-pentamethylnaphthaleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 87186Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of AlCl3 (2.88 g; 21.6 mmol) in methylene chloride (5 ml) was added over 15 minutes a solution of 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydro-naphthalene (4.0 g; 20 mmol) and acetyl chloride (1.6 ml; 21.6 mmol) in methylene chloride (20 ml) at 0° C. The reaction mixture was stirred for 30 minutes and ice cooled water (50 ml) was added. The organic phase was separated and the water phase was further extracted with methylene chloride (3×30 ml). The combined organic phases were first washed with brine then dried before evaporated. The residue was purified by column chromatography using hexane:methylene chloride (1:1) to give the title compound in 4.9 g (100%) yield.

Workup

  1. additionwas added
  2. customThe organic phase was separated
  3. extractionthe water phase was further extracted with methylene chloride (3×30 ml)
  4. washThe combined organic phases were first washed with brine
  5. customthen dried
  6. custombefore evaporated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1d0eb19cae354cfdade541f4041e83cd
Source dataset
uspto-grants-2001_08
Patent number
US06274608B1

Linked notes

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