Acetyl chloride → 1-(1,2,3,5,6,7-Hexahydro-s-indacen-4-yl)ethanone

HRID 1276540Notes

Reaction equation

HRID 1276540 reaction equation
[CH2:1]1[C:12]2[C:4](=[CH:5][C:6]3[CH2:7][CH2:8][CH2:9][C:10]=3[CH:11]=2)[CH2:3][CH2:2]1.[C:13](Cl)(=[O:15])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[CH2:3]1[C:4]2[C:12](=[C:11]([C:13](=[O:15])[CH3:14])[C:10]3[CH2:9][CH2:8][CH2:7][C:6]=3[CH:5]=2)[CH2:1][CH2:2]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 1363211,2,3,5,6,7-Hexahydro-s-indaceneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3826691-(1,2,3,5,6,7-Hexahydro-s-indacen-4-yl)ethanone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 1,2,3,5,6,7-Hexahydro-s-indacene (30 grams) and acetyl chloride (14.2 mL) in 120 mL of benzene at 0° C. was added 30 grams of aluminum chloride over a period of 1 hour. The cooling bath was removed and the solution was warmed to room temperature and stirred for 4 hours. The deep red mixture was then poured onto a mixture of 270 grams of ice and 50 mL of concentrated hydrochloric acid. The layers were separated and the aqueous phase was extracted with diethyl ether. The combined organic phases were washed with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford an orange solid which was recrystallized from hexane to give 34 grams of the title compound, m.p. 69.1-76.1° C.

Workup

  1. customThe cooling bath was removed
  2. additionThe deep red mixture was then poured onto a mixture of 270 grams of ice and 50 mL of concentrated hydrochloric acid
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with diethyl ether
  5. washThe combined organic phases were washed with saturated sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford an orange solid which
  9. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-54214663314b4574aadeed09f237f83b
Source dataset
uspto-grants-2000_12
Patent number
US06166064

Reaction notes

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