Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)- → HCID 18349868, compound

HRID 484368Notes

Reaction equation

HRID 484368 reaction equation
[C:1]([C:4]1[C:13]([CH3:14])=[CH:12][C:11]2[C:10]([CH3:16])([CH3:15])[CH2:9][CH2:8][C:7]([CH3:18])([CH3:17])[C:6]=2[CH:5]=1)(=[O:3])C.Cl[O-].[Na+].S(=O)(O)[O-:23].[Na+]>O1CCOCC1>[CH3:14][C:13]1[C:4]([C:1]([OH:23])=[O:3])=[CH:5][C:6]2[C:7]([CH3:17])([CH3:18])[CH2:8][CH2:9][C:10]([CH3:16])([CH3:15])[C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 87186Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-HCID 23665760Sodium Hypochlorite2×HCID 23665763Sodium Bisulfite

Product 1

HCID 18349868HCID 18349868, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 8.2 g (0.0336 mol) of 2-acetyl-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene, 90 ml of 1.19M (0.107 mol) aqueous sodium hypochlorite and 10 ml of dioxane was stirred at room temperature for 0.5 hours and at 60° C. for 2 hours. A further 70 ml of 1.19M (0.0833 mol) of aqueous sodium hypochlorite was then added to the reaction mixture and the mixture stirred at 70° C. for 1 hours. The reaction mixture was then cooled and treated with aqueous sodium bisulfite solution until the mixture was negative to starch/iodide paper. The mixture was washed with ether and then acidified with H2SO4. The mixture was extracted with three portions of ether and the ether extracts were then combined and washed successively with water and saturated NaCl solution and then dried (MgSO4). The ether solution was then concentrated and the title compound obtained as colorless crystals by recrystallization from cold ether. PMR (CDCl3): δ 1.29 (6H, s), 1.30 (6H, s), 1.69 (4H, s), 2.60 (3H, s), 7.17 (1H, s), 7.26 (1H, s).

Workup

  1. stirringthe mixture stirred at 70° C. for 1 hours
  2. temperatureThe reaction mixture was then cooled
  3. washThe mixture was washed with ether
  4. extractionThe mixture was extracted with three portions of ether
  5. washwashed successively with water and saturated NaCl solution
  6. dry with materialdried (MgSO4)
  7. concentrationThe ether solution was then concentrated

Sources & evidence

ORD record
ord-f13b9714458246f7954e5fa03afdbe28
Source dataset
uspto-grants-1993_07
Patent number
US05231113

Reaction notes

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