5-Benzoyl-6-hydroxy-2,3-dihydro-1H-indene-1-carboxylic acid → HCID 54088426, compound

HRID 1680265Notes

Reaction equation

HRID 1680265 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[OH:18])[CH:14]([C:19]([OH:21])=[O:20])[CH2:13][CH2:12]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)CCC.S(=O)(=O)(O)O>[CH2:9]([O:20][C:19]([CH:14]1[C:15]2[C:11](=[CH:10][C:9]([C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:17]([OH:18])[CH:16]=2)[CH2:12][CH2:13]1)=[O:21])[CH2:1][CH2:2][CH3:3]

Participants

4

Reactant 1

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

Product 1

HCID 54088426HCID 54088426, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 2631-ButanolSolvent

Procedure

A solution of 12 g of 5-benzoyl-6-hydroxy-indane-1-carboxylic acid in 100 ml of n-butanol and 8 drops of concentrated sulphuric acid is boiled for 6 hours under reflux in an anhydrous atmosphere. It is then evaporated to a volume of approx. 20 ml in vacuo and the evaporation residue is partitioned between 3 times 100 ml of methylene chloride and 3 times 100 ml of water. The organic phases are dried over sodium sulphate and evaporated in vacuo. The evaporation residue, when crystallised from cold ether-petroleum ether, gives 5-benzoyl-6-hydroxy-indane-1-carboxylic acid n-butyl ester in the form of yellow platelets of melting point 43°-44° C.

Workup

  1. temperatureunder reflux in an anhydrous atmosphere
  2. customIt is then evaporated to a volume of approx. 20 ml in vacuo
  3. customthe evaporation residue is partitioned between 3 times 100 ml of methylene chloride and 3 times 100 ml of water
  4. dry with materialThe organic phases are dried over sodium sulphate
  5. customevaporated in vacuo
  6. customThe evaporation residue, when crystallised from cold ether-petroleum ether

Sources & evidence

ORD record
ord-68212465eb3f497caa3fe353d549b79f
Source dataset
uspto-grants-1981_06
Patent number
US04272547

Reaction notes

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