Trifluoroacetic acid → HCID 178501272, compound

HRID 1035714Notes

Reaction equation

HRID 1035714 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 178501274HCID 178501274, compound

Product 1

HCID 178501272HCID 178501272, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

0.6 g of tert-butyl cis-4-(4-methoxycarbonylcyclohexyloxy)benzoate (1.79 mmol, 1 eq.) is placed in 2.5 mL of dichloromethane. The reaction medium is cooled to a temperature of 4° C. with stirring in an ice bath. 1 mL of trifluoroacetic acid (13.46 mmol, 7.5 eq.) is added and the ice bath is removed. After stirring for 5 hours at room temperature, the medium is concentrated, taken up in diethyl ether, drained and filtered to give 0.30 g of cis-4-(4-methoxycarbonylcyclohexyloxy)benzoic acid. M+H+=279.

Workup

  1. customthe ice bath is removed
  2. stirringAfter stirring for 5 hours at room temperature
  3. concentrationthe medium is concentrated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-9cda77603b9146a0b856989aa97d9d11
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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