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

HRID 2308951Notes

Reaction equation

HRID 2308951 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[C:5](Cl)(=[O:7])[CH3:6].[CH2:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1.Cl>C1C=CC=CC=1>[C:5]([C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[CH2:9][CH2:10][CH2:11]2)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 10326IndaneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2339761-(2,3-Dihydro-1H-inden-5-yl)ethan-1-oneYield 66.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
6.5 °C

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. customthen, the mixture is partitioned with ice (200 g) and 6N hydrochloric acid (100 ml)
  2. customthe organic phase is separated
  3. extractionthe aqueous phase is extracted with benzene
  4. customThe organic benzene layers are collected
  5. washwashed until neutral,
  6. customdried on MgSO4
  7. customthe excess solvent is evaporated under vacuum
  8. distillationThe residue (28.5 g) is distilled in high vacuum (1 mmHg)
  9. customthe fractions with b.p. 80°-85° C. are collected

Sources & evidence

ORD record
ord-79823018577847c1b1f042019a1fcc20
Source dataset
uspto-grants-1987_09
Patent number
US04692447

Reaction notes

Loading…