Indane → 5-(3-Chloropropionyl)indan

HRID 1276537Notes

Reaction equation

HRID 1276537 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Cl:10][CH2:11][CH2:12][C:13](Cl)=[O:14].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:10][CH2:11][CH2:12][C:13]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[CH2:1][CH2:2][CH2:3]2)=[O:14]

Participants

5

Reactant 3

HCID 10326IndaneHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 32867585-(3-Chloropropionyl)indanYield 53.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of indane (300 grams) and 3-chloropropionoyl chloride (323 grams) in methylene chloride (2 L) at 0° C. was added aluminum chloride (376 grams) over a period of 3 hours. Once the addition was complete, the cooling bath was removed and the mixture was warmed to room temperature and stirred until hydrogen chloride evolution ceased. The reaction was quenched by pouring onto a mixture of 3.5 kg of ice and 700 mL of concentrated hydrochloric acid. The layers were separated, and the aqueous phase was extracted with methylene chloride. The combined methylene chloride layers were washed with water, saturated sodium bicarbonate solution and brine. The organic phase was dried with anhydrous sodium sulfate and concentrated in vacuo. The residue was recrystallized from hexane to afford 282 grams of a yellow solid, m.p. 63.5-65.1° C.

Workup

  1. additionOnce the addition
  2. customthe cooling bath was removed
  3. customThe reaction was quenched
  4. additionby pouring onto a mixture of 3.5 kg of ice and 700 mL of concentrated hydrochloric acid
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with methylene chloride
  7. washThe combined methylene chloride layers were washed with water, saturated sodium bicarbonate solution and brine
  8. dry with materialThe organic phase was dried with anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-a1c980a954c642efb7db567bbfe418f9
Source dataset
uspto-grants-2000_12
Patent number
US06166064

Reaction notes

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