Sodium Hydroxide → 2-(4-Chloro-6-fluoro-1-hydroxy-1-indanyl)acetic acid

HRID 726148Notes

Reaction equation

HRID 726148 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2([CH2:13][C:14]([O:16]CC)=[O:15])[OH:12].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2([CH2:13][C:14]([OH:16])=[O:15])[OH:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10978626Ethyl 2-(4-chloro-6-fluoro-1-hydroxy-1-indanyl)acetate

Product 1

HCID 110860282-(4-Chloro-6-fluoro-1-hydroxy-1-indanyl)acetic acidYield 102.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-(4-chloro-6-fluoro-1-hydroxy-1-indanyl)acetate (14.5 g, 0.05 mol), 1N sodium hydroxide (52 ml) and absolute ethanol (100 ml) was stirred for 18 h at room temperature. The mixture was concentrated in vacuo, diluted with H2O and washed with diethyl ether. The aqueous phase was neutralised with 1.0N hydrochloric acid (52 ml) and extracted with diethyl ether. The diethyl ether extracts were dried over sodium sulphate, filtered and concentrated in vacuo to give 12.5 g (96%) of crude 2-(4-chloro-6-fluoro-1-hydroxy-1-indanyl)acetic acid. This material was used immediately without further purification.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with H2O
  3. washwashed with diethyl ether
  4. extractionextracted with diethyl ether
  5. dry with materialThe diethyl ether extracts were dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c54cfe93aee64559ac7ef51915a84c96
Source dataset
uspto-grants-1998_01
Patent number
US05708033

Reaction notes

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