Acetic Anhydride → 1-(2,3-Dihydro-1H-inden-5-yl)ethan-1-one

HRID 2206669Notes

Reaction equation

HRID 2206669 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH3:10][C:11](OC(C)=O)=[O:12].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:11](=[O:12])[CH3:10])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 10326IndaneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2339761-(2,3-Dihydro-1H-inden-5-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of indane (1, 12.25 mL, 0.10 mol) and Ac2O (11.34 mL, 0.12 mol) was added dropwise for 1 h to a slurry of AlCl3 (26.7 g, 0.2 mol) in DCM (100 mL) at 0° C. The reaction mixture was warmed up to room temperature and stirred for 15 h. The mixture was cooled to 0° C. and quenched by slow addition of water (20-30 mL) and 1 M HCl (50 mL). The organic layer was separated, washed with brine and saturated NaHCO3 solution, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude product 2 was dried under high vacuum and used without further purification (16.1 g, 0.10 mol, 100%).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customquenched by slow addition of water (20-30 mL) and 1 M HCl (50 mL)
  3. customThe organic layer was separated
  4. washwashed with brine and saturated NaHCO3 solution
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dry with materialThe crude product 2 was dried under high vacuum
  9. customused without further purification (16.1 g, 0.10 mol, 100%)

Sources & evidence

ORD record
ord-19fadf0f43aa4694ab7341822b283fc3
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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