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

HRID 869852Notes

Reaction equation

HRID 869852 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%

Procedure

To a stirred aqueous sodium hypochlorite solution (2230 ml, 1.80 mmol, 6□) at 55□ was added 1-(2,3-dihydro-1H-inden-6-yl)ethanone (120.0 g, 0.75 mol) and the mixture was stirred at 55□ 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. filtrationThe produced precipitate was filtered
  2. washwashed several times with water
  3. customdried

Sources & evidence

ORD record
ord-b55a6a3c2a5a49118e82c2685b28bfbe
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

Loading…