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

HRID 576297Notes

Reaction equation

HRID 576297 reaction equation
BrBr.[OH-].[K+].[CH2:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14](=[O:16])C)=[CH:11][CH:12]=2)[CH2:7][CH2:6]1.[O-:17]S([O-])(=S)=O.[Na+].[Na+].Cl>O>[CH2:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([OH:16])=[O:17])=[CH:11][CH:12]=2)[CH2:7][CH2:6]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 2339761-(2,3-Dihydro-1H-inden-5-yl)ethan-1-one

Product 1

HCID 2328412,3-dihydro-1H-indene-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

Bromine (20.5 mL, 0.4 mol) was added to a solution of KOH (72.9 g, 1.3 mol) in water (250 mL) at 0° C. To the resulting solution was slowly added compound 2 (16.0 g, 0.1 mol) at 0° C. The reaction mixture was heated at 55° C. overnight and quenched with Na2S2O3 (14.8 g, 0.094 mol). The mixture was acidified to pH 2-3 with conc. HCl (40˜50 mL). The precipitate was collected by filtration, and washed with water. The crude product 3 was dried under high vacuum and used without further purification (15.4 g, 0.095 mol, 95%).

Workup

  1. customat 0° C
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. dry with materialThe crude product 3 was dried under high vacuum
  5. customused without further purification (15.4 g, 0.095 mol, 95%)

Sources & evidence

ORD record
ord-2800f530bd034ee4ae7cce69e5d786e4
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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