Trifluoroacetic acid → 4-(Adamantan-2-yl(benzyloxy)methyl)-3-chlorobenzoic acid

HRID 1849751Notes

Reaction equation

HRID 1849751 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[CH:11]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:12]1[CH:24]=[CH:23][C:15]([C:16]([O:18]C(C)(C)C)=[O:17])=[CH:14][C:13]=1[Cl:25])[CH2:8]2.FC(F)(F)C(O)=O>ClCCl>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[CH:11]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:12]1[CH:24]=[CH:23][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=1[Cl:25])[CH2:8]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86703632Tert-butyl 4-(adamantan-2-yl(benzyloxy)methyl)-3-chlorobenzoate

Product 1

HCID 867036334-(Adamantan-2-yl(benzyloxy)methyl)-3-chlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl 4-(adamantan-2-yl(benzyloxy)methyl)-3-chlorobenzoate (0.43 g, 1.05 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (1 mL) and the reaction mixture was stirred for 2 hour at ambient temperature. Removal of all volatiles under reduced pressure gave 4-(adamantan-2-yl(benzyloxy)methyl)-3-chlorobenzoic acid as an oily residue (0.43 g, quant.), which was used without further purification.

Workup

  1. customRemoval of all volatiles under reduced pressure

Sources & evidence

ORD record
ord-f7f28d0290684939bfa7014f01929c35
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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