1-(2,3-Dihydro-1H-inden-5-yl)ethan-1-one → 2,3-dihydro-1H-indene-5-carboxylic acid

HRID 1847899Notes

Reaction equation

HRID 1847899 reaction equation
Cl[O-].[Na+].[CH2:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13](=[O:15])C)[CH:11]=2)[CH2:6][CH2:5]1.C([O-])(O)=[O:17].[Na+]>>[CH2:6]1[C:7]2[C:12](=[CH:11][C:10]([C:13]([OH:15])=[O:17])=[CH:9][CH:8]=2)[CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 2339761-(2,3-Dihydro-1H-inden-5-yl)ethan-1-oneHCID 516892Sodium BicarbonateHCID 23665760Sodium Hypochlorite

Product 1

HCID 2328412,3-dihydro-1H-indene-5-carboxylic acidYield 99%

Conditions

Temperature
55 °C

Procedure

To a stirred aqueous sodium hypochlorite solution (2230 ml, 1.80 mmol, 6%) at 55° C. was added 1-(2,3-dihydro-1H-inden-6-yl)ethanone (120.0 g, 0.75 mol) and the mixture was stirred at 55° C. for 2 h. After cooling to room temperature, saturated NaHCO3 solution was added until the solution became clear. The produced precipitate was filtered, washed several times with water and dried to afford the desired product (120.0 g, 99%). 1H NMR (CDCl3, 300 MHz) δ 2.07-2.17 (m, 2H), 2.96 (t, J=7.5 Hz, 4H), 7.30 (d, J=7.8, 1H), 7.91 (d, J=7.8, 1H), 7.96 (s, 1H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe produced precipitate was filtered
  3. washwashed several times with water
  4. customdried

Sources & evidence

ORD record
ord-a6ced17d52154c9cb7d097ee5f2ee6c6
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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