Acetyl chloride → HCID 20077196, compound

HRID 1289446Notes

Reaction equation

HRID 1289446 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]1[CH2:14][C:15]([O:17][CH3:18])=[O:16].[C:19](Cl)(=[O:21])[CH3:20]>C(Cl)Cl>[C:19]([C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[CH2:5][CH:6]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:7]2)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 14090225Methyl (2,3-dihydro-1H-inden-2-yl)acetate

Product 1

HCID 20077196HCID 20077196, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Added to 160 ml of methylene chloride were 52.9 g (0.388 mol) of anhydrous aluminum chloride. While chilling with ice water, a solution of 25.03 g (0.132 mol) of methyl (indan-2-yl)acetate in 40 ml of methylene chloride was added dropwise to the solution, followed by the addition of 13.1 ml (0.185 mol) of acetyl chloride. After stirring the mixture at the same temperature for 40 minutes, the reaction mixture was poured into ice water to take out an organic layer separated. After the organic layer was washed with water and dried, the solvent was distilled off under reduced pressure. The resultant residue was purified by column chromatography on silica gel (ethyl acetate-hexane=1:2), thereby obtaining 27.8 g of an oily substance. Yield: 91%.

Workup

  1. customseparated
  2. washAfter the organic layer was washed with water
  3. customdried
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resultant residue was purified by column chromatography on silica gel (ethyl acetate-hexane=1:2)
  6. customobtaining 27.8 g of an oily substance

Sources & evidence

ORD record
ord-023ea0be0b2840d58d75a70c83a3d725
Source dataset
uspto-grants-1998_05
Patent number
US05750524

Reaction notes

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