Sodium Hydroxide → 1-benzyl-2,3-dihydro-1H-indene-1-carboxylic acid

HRID 452554Notes

Reaction equation

HRID 452554 reaction equation
[CH2:1]([C:8]1([C:17]([O:19]C)=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[CH2:1]([C:8]1([C:17]([OH:19])=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66923500Methyl 1-benzylindane-1-carboxylate

Product 1

HCID 654070031-benzyl-2,3-dihydro-1H-indene-1-carboxylic acidYield 101.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 1-benzylindane-1-carboxylate (2.5 g, 9.4 mmol) from Step B was dissolved in a solution of 23 mL methanol and 23 mL water. Sodium hydroxide (0.940 g, 23.5 mmol) was added to the reaction. The reaction was refluxed and stirred for 90 minutes and then quenched with 100 mL of 1N HCl and extracted with diethyl ether (3×50 mL). The combined organic washings were dried over MgSO4 and evaporated to furnish 1-benzylindane-1-carboxylic acid (2.4 g, 100%) as a yellow oil that was pure enough to be used in the next step.

Workup

  1. temperatureThe reaction was refluxed
  2. customquenched with 100 mL of 1N HCl
  3. extractionextracted with diethyl ether (3×50 mL)
  4. dry with materialThe combined organic washings were dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-e1fc914c674c47a3ae604d9aff74c076
Source dataset
uspto-grants-2013_07
Patent number
US08492387B2

Reaction notes

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