Hydrochloric Acid → 2,3-dihydro-1H-indene-5-carboxylic acid

HRID 22653Notes

Reaction equation

HRID 22653 reaction equation
Cl[O-].[Na+].[CH2:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:15])C)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.S(=O)(O)[O-:17].[Na+].Cl>O>[CH2:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([OH:15])=[O:17])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2339761-(2,3-Dihydro-1H-inden-5-yl)ethan-1-oneHCID 23665760Sodium HypochloriteHCID 23665763Sodium Bisulfite

Product 1

HCID 2328412,3-dihydro-1H-indene-5-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

To a stirred 6% aqueous sodium hypochlorite solution in an oil bath to 55° C. is added 1-indane-5-yl-ethanone (1.0 g, 6.2 mmol). The solution is stirred at 55° C. for 2 h, followed by cooling to rt. Solid sodium bisulfite is added until the solution becomes clear. The mixture is diluted with water, followed by aqueous hydrochloric acid (6.0 M). The solid that forms is filtered and washed several times with water. The solid is dried under high vacuum at 60° C. for 5 h to afford 5-indancarboxylic acid as a white solid (0.96 g, 95%): 1H NMR (CDCl3) δ 8.0, 7.9, 7.3, 3.0, 2.1.

Workup

  1. temperatureby cooling to rt
  2. filtrationThe solid that forms is filtered
  3. washwashed several times with water
  4. customThe solid is dried under high vacuum at 60° C. for 5 h

Sources & evidence

ORD record
ord-d2af36b00ad946f0b17305882efe727c
Source dataset
uspto-grants-2005_02
Patent number
US06849620B2

Reaction notes

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