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

HRID 2308952Notes

Reaction equation

HRID 2308952 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH2:8][CH2:7]2)(=O)[CH3:2].Cl.[NH2:14][OH:15].C([O-])(=O)C.[K+]>C(O)C>[C:1](=[N:14][OH:15])([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH2:8][CH2:7]2)[CH3:2]

Participants

5

Reactant 3

HCID 2339761-(2,3-Dihydro-1H-inden-5-yl)ethan-1-oneHCID 443297Hydroxyamine hydrochlorideHCID 517044Potassium Acetate

Product 1

HCID 28250475-ACETOHYDROXIMOYLINDANEYield 91.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Anhydrous aluminum trichloride (25 g) is added dropwise to a stirred mixture of acetylchloride (11.8 g), indane (24 g) and dry benzene (100 ml) stirred at 5-8° C. The stirring is continued for 6 hours at this temperature until the evolution of hydrogen chloride is over; then, the mixture is partitioned with ice (200 g) and 6N hydrochloric acid (100 ml), the organic phase is separated, the aqueous phase is extracted with benzene. The organic benzene layers are collected, washed until neutral, dried on MgSO4 and the excess solvent is evaporated under vacuum. The residue (28.5 g) is distilled in high vacuum (1 mmHg) and the fractions with b.p. 80°-85° C. are collected affording 16 g of 5-acetylindane. I.R.=1680 cm-1. H-NMR (CDCl3 /TMS): 7.1-7.8 (m, 3H, Ar); 2.9 (t, 4H); 2.55 (s, 3H, CH3); 1.9-2.4 (m, 2H). A solution of 5-acetylindane (15 g) in ethanol (50 ml) is treated with a solution of hydroxylamine hydrochloride (15 g) and potassium acetate (21.5 g) in ethanol (50 ml) for 20 minutes at the reflux temperature. The excess of the solvent is evaporated in vacuum and the mixture is diluted with water. The precipitate is collected by filtration affording 15.01 g of 5-acetylindane oxime m.p. 104° C. I.R.=3200 cm-1. H-NMR (CDCl3 /TMS): 8.15 (s, 1H, N--OH); 2.3 (s, 3H, CH3).

Workup

  1. customThe excess of the solvent is evaporated in vacuum
  2. additionthe mixture is diluted with water
  3. filtrationThe precipitate is collected by filtration

Sources & evidence

ORD record
ord-8339e7e863d448c1a45d855cfa9ce711
Source dataset
uspto-grants-1987_09
Patent number
US04692447

Reaction notes

Loading…