Trifluoroacetic acid → HCID 178501273, compound

HRID 1035696Notes

Reaction equation

HRID 1035696 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:24]=[CH:23][C:15]([C:16]([O:18][C:19](C)(C)C)=[O:17])=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:19][O:18][C:16]([C@H:15]1[CH2:23][CH2:24][C@H:12]([O:11][C:8]2[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=2)[CH2:13][CH2:14]1)=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178501275HCID 178501275, compound

Product 1

HCID 178501273HCID 178501273, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

1.6 g of tert-butyl trans-4-(4-methoxycarbonylcyclohexyloxy)benzoate (4.78 mmol, 1 eq.) are placed in dichloromethane. The reaction medium is cooled to a temperature of 4° C. with stirring in an ice bath. 3 mL of trifluoroacetic acid (40.39 mmol, 8.44 eq.) are added and the ice bath is removed. After stirring for 17 hours at room temperature, the medium is concentrated, taken up in diethyl ether and filtered to give 1.0 g of trans-4-(4-methoxycarbonylcyclohexyloxy)benzoic acid.

Workup

  1. customthe ice bath is removed
  2. stirringAfter stirring for 17 hours at room temperature
  3. concentrationthe medium is concentrated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-48b9078f3a7e404ba978771a1e4e70d0
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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