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

HRID 2067175Notes

Reaction equation

HRID 2067175 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[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.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(OCC)(=O)C.C(Cl)Cl>[CH3:16][C:12]1[C:13]([C:1](=[O:3])[CH3:2])=[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 811871,2,3,4-Tetrahydro-1,1,4,4,6-pentamethylnaphthaleneHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 87186Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-Yield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 250 ml three-necked round bottomed flask fitted with a magnetic stirring bar and a reflux condenser containing acetyl chloride (2.3 g, 29.7 mmol) and 50 ml of DCM was added 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene 1b (5 g, 24.8 mmol) followed by slow addition (ca. 0.5 g portions) of AlCl3 (7.5 g, 56.2 mmol). The brown mixture was stirred for 30 min and then heated at reflux for 15 min. Additional AlCl3 (1-2 g) was necessary to effect the completion of the reaction. The cooled reaction mixture was poured into 200 ml of vigorously stirred ice water followed by acidification with 20% aqueous hydrochloric acid 50 ml and addition of 100 ml of ethyl acetate. Stirring was continued until the organic layer was yellow 15 min. The organic layer was extracted with ethyl acetate (2×100 ml), dried over MgSO4, filtered and concentrated in vacuo. Kugelrohr distillation (80-120° C., 3×10−4 torr) gave an analytically pure sample of 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-yl)ethanone 5.31 g (88%) as a white solid; m.p. 54-56° C.

Workup

  1. customTo a 250 ml three-necked round bottomed flask fitted with a magnetic stirring bar and a reflux condenser
  2. temperatureheated
  3. temperatureat reflux for 15 min
  4. customthe completion of the reaction
  5. customThe cooled reaction mixture
  6. stirringStirring
  7. waitwas yellow 15 min
  8. extractionThe organic layer was extracted with ethyl acetate (2×100 ml)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. distillationKugelrohr distillation (80-120° C., 3×10−4 torr)

Sources & evidence

ORD record
ord-2dff239a7bb64dbdae023cfc9b7bb927
Source dataset
uspto-grants-2012_10
Patent number
US08293803B2

Reaction notes

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