Sodium Hydroxide → 2-(4,6-Difluoro-1-hydroxy-1-indanyl)acetic acid

HRID 362819Notes

Reaction equation

HRID 362819 reaction equation
[F: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>[F: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 11780116Ethyl 2-(4,6-difluoro-1-hydroxy-1-indanyl)acetate

Product 1

HCID 109112982-(4,6-Difluoro-1-hydroxy-1-indanyl)acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-(4,6-difluoro-1-hydroxy-1-indanyl)acetate (12.0 g 0.047 mol) and 1.0N sodium hydroxide (48 mL, 0.048 mol, Universal Scientific Supply Co.) in ethanol (75 mL) was stirred for 18 h at ambient temperature. The reaction mixture was concentrated in vacuo, diluted with water and washed with diethyl ether. The aqueous phase was neutralized with 1.0N hydrochloric acid (48 mL, 0.048 mol, Universal Scientific Supply Co.) and extracted with diethyl ether. The diethyl ether extract was dried over sodium sulfate, filtered and concentrated in vacuo to give a quantitative yield of crude 2-(4,6-difluoro-1-hydroxy-1-indanyl)acetic acid. This material was used immediately without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with water
  3. washwashed with diethyl ether
  4. extraction) and extracted with diethyl ether
  5. extractionThe diethyl ether extract
  6. dry with materialwas dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-923fb04ca4a44f18985be10734efe34d
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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