HCID 54474250, compound → HCID 23457895, compound

HRID 1680274Notes

Reaction equation

HRID 1680274 reaction equation
C[O:2][C:3]([C:5]1([CH2:23][OH:24])[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>[OH:24][CH2:23][C:5]1([C:3]([OH:4])=[O:2])[C:13]2[C:8](=[CH:9][C:10]([C:15](=[O:22])[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:11]([OH:14])[CH:12]=2)[CH2:7][CH2:6]1

Participants

4

Reactant 1

HCID 54474250HCID 54474250, compound

Product 1

HCID 23457895HCID 23457895, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2.8 g of 1-hydroxymethyl-5-benzoyl-6-hydroxy-indane-1-carboxylic acid methyl ester in 12 ml of 2 N sodium hydroxide solution and 50 ml of methanol is heated to the reflux temperature for 5 hours. It is then evaporated in vacuo to a volume of approx. 10 ml and the evaporation residue is partitioned between twice 50 ml of water and 50 ml of ether. The aqueous phases are combined, acidified to pH 1 with concentrated hydrochloric acid and extracted with twice 50 ml of ether. The organic extracts are washed until neutral, dried over sodium sulphate and evaporated to dryness in vacuo. Chromatography of the evaporation residue on 100 g of silica gel using ether as the eluting agent gives pure 1-hydroxymethyl-5-benzoyl-6-hydroxy-indane-1-carboxylic acid in the form of yellow crystals of melting point 104°-110° C.

Workup

  1. customIt is then evaporated in vacuo to a volume of approx. 10 ml
  2. customthe evaporation residue is partitioned between twice 50 ml of water and 50 ml of ether
  3. extractionextracted with twice 50 ml of ether
  4. washThe organic extracts are washed until neutral,
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-2e68537f8e684dd5b7d875079fce328e
Source dataset
uspto-grants-1981_06
Patent number
US04272547

Reaction notes

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