Sodium Hydroxide → 5-Benzoyl-6-hydroxy-2,3-dihydro-1H-indene-1-carboxylic acid

HRID 1438925Notes

Reaction equation

HRID 1438925 reaction equation
C[O:2][C:3]([CH:5]1[C:13]2[C:8](=[CH:9][C:10]([C:15](=[O:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:11]([OH:14])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>CO>[C:15]([C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][C:11]=1[OH:14])[CH:5]([C:3]([OH:4])=[O:2])[CH2:6][CH2:7]2)(=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54109752HCID 54109752, compound

Product 1

HCID 688795-Benzoyl-6-hydroxy-2,3-dihydro-1H-indene-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 8.2 g of 5-benzoyl-6-hydroxy-indane-1-carboxylic acid methyl ester in 150 ml of methanol is mixed with 20 ml of 2 N sodium hydroxide solution and the mixture is boiled for 3 hours under reflux. It is then evaporated to dryness in vacuo and the evaporation residue is partitioned between 100 ml of 2 N hydrochloric acid and 3 times 100 ml of methylene chloride. The organic phases are washed until neutral, dried over sodium sulphate, treated with active charcoal and evaporated in vacuo. The evaporation residue, when crystallized from ethanol-petroleum ether, gives 5-benzoyl-6-hydroxy-indane-1-carboxylic acid in the form of yellow platelets of melting point 185-7° C.

Workup

  1. temperatureunder reflux
  2. customIt is then evaporated to dryness in vacuo
  3. customthe evaporation residue is partitioned between 100 ml of 2 N hydrochloric acid and 3 times 100 ml of methylene chloride
  4. washThe organic phases are washed until neutral,
  5. dry with materialdried over sodium sulphate
  6. additiontreated with active charcoal
  7. customevaporated in vacuo
  8. customThe evaporation residue, when crystallized from ethanol-petroleum ether

Sources & evidence

ORD record
ord-7b2cf0fbcf974122a0e62eeb598eda15
Source dataset
uspto-grants-1977_11
Patent number
US04057573

Reaction notes

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