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

HRID 468497

Reaktionsgleichung

Reaktionsgleichung von HRID 468497
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 2339761-(2,3-Dihydro-1H-inden-5-yl)ethan-1-oneAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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 3 h. 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%). 1H NMR (400 MHz, CDCl3) δ 2.08-2.15 (m, 2H), 2.58 (s, 3H), 2.95 (t, J=7.2, 4H), 7.28 (d, J=8.0, 1H), 7.75 (d, J=8.0, 1H) 7.82 (s, 1H).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-e82991cac1264219a766bf98e3a9ecbf
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623905B2

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