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

HRID 2038111Notes

Reaction equation

HRID 2038111 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:10](OC(=O)C)(=[O:12])[CH3:11].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10](=[O:12])[CH3:11])[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-oneYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,3-dihydro-1H-indene (100.0 g, 0.85 mol) and acetic anhydride (104.2 g, 1.35 mol) was added drop-wise to a slurry of AlCl3(272.0 g, 2.04 mol) in CH2Cl2 (1000 ml) at 0° C. over a period of 3h. The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 15 h. Then the reaction mixture was poured into ice water (500 mL) and extracted with ethyl acetate (500 mL×3). The combined organic layers were washed with brine (500 mL), dried over Na2SO4 and evaporated in vacuo. The residue that was purified by column chromatography (petroleum ether:ethyl acetate=20:1) to give the product (120.0 g, 88%). 1 H NMR (400 MHz, CDCl3) δ 2.08-2.15(m, 2H), 2.58(s, 3H), 2.95(t, J=7.2, 4 H), 7.28(d, J=8.0, 1H), 7.75(d, J=8.0, 1H) 7.82(s, 1H).

Workup

  1. extractionextracted with ethyl acetate (500 mL×3)
  2. washThe combined organic layers were washed with brine (500 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe residue that was purified by column chromatography (petroleum ether:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-b1e45a839248466c80ca84c662871159
Source dataset
uspto-grants-2013_11
Patent number
US08575209B2

Reaction notes

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