Ethanol → (RS)-(2,6-difluoro-3-hydroxy-phenyl)-ethoxy-acetic acid ethyl ester

HRID 1247382Notes

Reaction equation

HRID 1247382 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[CH:10]([O:14][CH2:15][CH3:16])[C:11]([OH:13])=[O:12].[CH3:17][CH2:18]O>Cl>[CH2:17]([O:12][C:11](=[O:13])[CH:10]([C:3]1[C:4]([F:9])=[CH:5][CH:6]=[C:7]([OH:8])[C:2]=1[F:1])[O:14][CH2:15][CH3:16])[CH3:18]

Participants

4

Reactant 2

HCID 702Ethanol2×HCID 21905416(RS)-(2,6-difluoro-3-hydroxy-phenyl)-ethoxy-acetic acid

Product 1

HCID 69290130(RS)-(2,6-difluoro-3-hydroxy-phenyl)-ethoxy-acetic acid ethyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (RS)-(2,6-difluoro-3-hydroxy-phenyl)-ethoxy-acetic acid (14.8 g) in EtOH (200 ml) and 1.25 N HCl in EtOH (60 ml) was stirred over night at rt. The solvent was evaporated and the residue was purified by CC (AcOEt/Hept 1:1) to obtain 15.5 g (93%) of (RS)-(2,6-difluoro-3-hydroxy-phenyl)-ethoxy-acetic acid ethyl ester. Off-white solid. MS 258.9 ([M−H]−).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by CC (AcOEt/Hept 1:1)

Sources & evidence

ORD record
ord-6b88e7250ded4f7cb742cdba41489ec7
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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