1,1,1-Trifluorooctan-2-YL 2-fluoro-4-hydroxybenzoate → 4-(Octyloxy)benzoic acid

HRID 1728526Notes

Reaction equation

HRID 1728526 reaction equation
FC1C=C(O)C=CC=1C(OC(CCCCCC)C(F)(F)F)=O.C(OC1C=C[C:35]([C:38]2C=C[C:41]([C:44]([O:46][C:47]3[CH:52]=[CH:51][C:50]([C:53]([O:55]C(CCCCCC)C(F)(F)F)=[O:54])=[C:49](F)[CH:48]=3)=O)=[CH:40][CH:39]=2)=[CH:34][CH:33]=1)CCCCCCC>O1CCCC1>[CH2:44]([O:46][C:47]1[CH:48]=[CH:49][C:50]([C:53]([OH:55])=[O:54])=[CH:51][CH:52]=1)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:35][CH2:34][CH3:33]

Participants

4

Reactant 2

HCID 199208191,1,1-Trifluorooctan-2-YL 2-fluoro-4-hydroxybenzoateHCID 537499373-Fluoro-4-(1,1,1-trifluoro-2-octyloxycarbonyl)phenyl 4-octyloxybiphenyl-4'-carboxylate

Product 1

HCID 172314-(Octyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the 1,1,1-trifluoro-2-decyl-6-hydroxynaphthalene-2-carboxylate (0.5 g) obtained in (1) above, the 4-n-octyloxybenzoic acid (0.4 g) obtained in (2) above in tetrahydrofuran (40 ml) were added dicyclohexylcarbodiimide (0.45 g) and dimethylaminopyridine (0.05 g). The solution was stirred at room temperature overnight. The solution was distilled to remove the solvent. The residue was dissolved in dichloromethane (50 ml) and the solution was washed with dilute aqueous hydrochloric acid solution and water in this order. The organic layer collected was dried over anhydrous magnesium sulfate, and distilled to remove the solvent. The residue was purified by silica-gel column chromatography (developer: hexane/ethyl acetate=20/1) to obtain the titled compound (0.39 g) having specific rotation, [α]DD20 =+45.79°.

Sources & evidence

ORD record
ord-fdd2df0e504d4df08ae9aa70898a8166
Source dataset
uspto-grants-1994_07
Patent number
US05328641

Reaction notes

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