Acetyl chloride → Celestolide

HRID 1447781Notes

Reaction equation

HRID 1447781 reaction equation
[CH3:1][C:2]1([CH3:15])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:9]=2)[CH2:4][CH2:3]1.[C:16](Cl)(=[O:18])[CH3:17].[Cl-].[Al+3].[Cl-].[Cl-]>CCCCCC>[C:16]([C:6]1[CH:7]=[C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][C:2]2([CH3:15])[CH3:1])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 771541H-Indene, 6-(1,1-dimethylethyl)-2,3-dihydro-1,1-dimethyl-3×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 61585CelestolideYield 121.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of 1,1-dimethyl-6-t-butylindane (600 grams) and acetyl chloride (314 grams) is added over a 4 hour period at -10° C. to a slurry of aluminum chloride (534 grams), 1,1-dimethyl-6-t-butylindane (1420 grams) and n-hexane (400 grams). The resulting reaction mass is poured into 5 liters of ice water with vigorous stirring thereby forming 2 liquid layers. The bottom (aqueous) layer is discarded and the organic layer is washed twice with 2 liters of water. Distillation affords recovered 1,1-dimethyl-6-t-butylindane (1252 grams, 62% recovery) and 878 grams of 4-acetyl-6-t-butyl-1,1-dimethylindane (90% yield based on acetyl chloride, 95% yield based on consumed 1,1-dimethyl-6-t-butylindane.).

Workup

  1. customThe resulting reaction mass
  2. customthereby forming 2 liquid layers
  3. washthe organic layer is washed twice with 2 liters of water
  4. distillationDistillation
  5. customaffords

Sources & evidence

ORD record
ord-2cd9bdb8e14549c1b13af38aafc7fc05
Source dataset
uspto-grants-1979_12
Patent number
US04178311

Reaction notes

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