Sodium Hydroxide → 2-(6-Fluoro-1-hydroxy-1-indanyl)acetic acid

HRID 362808Notes

Reaction equation

HRID 362808 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH2:12][C:13]([O:15]CC)=[O:14])[OH:11])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH2:12][C:13]([OH:15])=[O:14])[OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23293626Ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate

Product 1

HCID 232935722-(6-Fluoro-1-hydroxy-1-indanyl)acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate (44.0 g, 0.18 mol), 1N sodium hydroxide (180 mL) and absolute ethanol (280 mL) was stirred for 18 h at room temperature. The mixture was concentrated in vacuo, diluted with H2O and extracted with diethyl ether. The aqueous phase was acidified (pH 3) with dilute hydrochloric acid and extracted with diethyl ether. The diethyl ether layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give 2-(6-fluoro-1-hydroxy-1-indanyl)acetic acid as an amber oil (37.7 g, 100%; Note: This compound spontaneously dehydrated upon standing at room temperature to a mixture of olefins unless immediately reacted with trifluoroacetic acid);

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with H2O
  3. extractionextracted with diethyl ether
  4. extractionextracted with diethyl ether
  5. washThe diethyl ether layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74a1dee3c35a44ea8752c514174a4516
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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