Trifluoroacetic acid → (1S,2S)-2-(4-Hydroxy-phenyl)-cyclopropanecarboxylic acid ethyl ester

HRID 471430Notes

Reaction equation

HRID 471430 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15]C(C)(C)C)=[CH:11][CH:10]=1)=[O:5])[CH3:2].FC(F)(F)C(O)=O>>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 72700304(1S,2S)-2-(4-tert-Butoxy-phenyl)-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 72700607(1S,2S)-2-(4-Hydroxy-phenyl)-cyclopropanecarboxylic acid ethyl esterYield 88.6%

Procedure

(1S,2S)-2-(4-tert-Butoxy-phenyl)-cyclopropanecarboxylic acid ethyl ester (10.5 g, 35.62 mmol) is dissolved in trifluoroacetic acid (15 mL, 195.6 mmol) and stirred for 5 minutes. The mixture is concentrated under vacuum, then reevaporated five times from dichloromethane. The residue is dissolved in boiling cyclohexane (20 mL) and then allowed to cool. The cyclohexane layer is decanted off and the operation repeated. The residue is dried under vacuum to give the title compound (yield 6.51 g).

Workup

  1. concentrationThe mixture is concentrated under vacuum
  2. customreevaporated five times from dichloromethane
  3. dissolutionThe residue is dissolved
  4. temperatureto cool
  5. customThe cyclohexane layer is decanted off
  6. customThe residue is dried under vacuum

Sources & evidence

ORD record
ord-14ffa82160224e4b8b8f6fb1ed4712ca
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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