Methanol → HCID 54114833, compound

HRID 1680280Notes

Reaction equation

HRID 1680280 reaction equation
S(=O)(=O)(O)O.[C:6]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][C:22]=1[OH:23])[CH:19]([CH2:24][C:25]([OH:27])=[O:26])[CH2:18][CH2:17]2)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[CH3:29]O>>[CH3:29][O:26][C:25](=[O:27])[CH2:24][CH:19]1[C:20]2[C:16](=[CH:15][C:14]([C:6](=[O:13])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[C:22]([OH:23])[CH:21]=2)[CH2:17][CH2:18]1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 23457882HCID 23457882, compound

Product 1

HCID 54114833HCID 54114833, compound

Procedure

0.5 ml of concentrated sulphuric acid is added to a solution of 1.4 g of 5-benzoyl-6-hydroxy-indane-1-acetic acid in 300 ml of absolute methanol and the mixture is heated to the reflux temperature for 8 hours, with exclusion of water. The reaction mixture is then evaporated in vacuo to a volume of 5 ml and partitioned between 20 ml of water and twice 20 ml of ether. The organic phases are combined, washed until neutral, dried over sodium sulphate and evaporated in vacuo. Distillation of the evaporation residue in a high vacuum gives, in the fraction boiling at 180° C./0.04 mm, 5-benzoyl-6-hydroxyindane-1-acetic acid methyl ester as a yellow oil which is identical with the product described in Example 22.

Workup

  1. customThe reaction mixture is then evaporated in vacuo to a volume of 5 ml
  2. custompartitioned between 20 ml of water and twice 20 ml of ether
  3. washwashed until neutral,
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo
  6. distillationDistillation of the evaporation residue in a high vacuum

Sources & evidence

ORD record
ord-e94b0fd2d4dc47a6874e855efbd5bfed
Source dataset
uspto-grants-1981_06
Patent number
US04272547

Reaction notes

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