1,1,1-Trifluorooctan-2-YL 6-hydroxynaphthalene-2-carboxylate → Benzoic acid, 4-((1-oxodecyl)oxy)-

HRID 1728527Notes

Reaction equation

HRID 1728527 reaction equation
OC1C=C2C(=CC=1)C=C(C(OC(CCCCCC)C(F)(F)F)=O)C=C2.FC1C=C(O)C=CC=1C(OC(CCCCCC)C(F)(F)F)=O.C(O[C:57]1[CH:62]=C[C:60]([C:63]2C=C[C:66]([C:69]([O:71][C:72]3[CH:77]=[CH:76][C:75]([C:78]([O:80]C(CCCCCC)C(F)(F)F)=[O:79])=[C:74](F)[CH:73]=3)=[O:70])=[CH:65][CH:64]=2)=[CH:59][CH:58]=1)CCCCCCC>O1CCCC1>[CH2:66]([C:69]([O:71][C:72]1[CH:77]=[CH:76][C:75]([C:78]([OH:80])=[O:79])=[CH:74][CH:73]=1)=[O:70])[CH2:65][CH2:64][CH2:63][CH2:60][CH2:59][CH2:58][CH2:57][CH3:62]

Participants

5

Reactant 3

HCID 157248111,1,1-Trifluorooctan-2-YL 6-hydroxynaphthalene-2-carboxylateHCID 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 3608562Benzoic acid, 4-((1-oxodecyl)oxy)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the 1,1,1-trifluoro-2-octyl 6-hydroxynaphthalene-2-carboxylate (0.6 g) obtained in (1) above and the 4-n-nonylcarbonyloxybenzoic acid (0.45 g) obtained in (2) above in tetrahydrofuran (40 ml) were added dicyclohexylcarbodiimide (0.45 g) and dimethylaminopyridine (0.05 g). The solution was stirred overnight and distilled to remove the solvent. The residue was dissolved in dichloromethane (40 ml) and washed with dilute aqueous hydrochloric acid solution and water, in this order. The solution 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 (0.05 g) having specific rotation, [α]D20 =+42.86°.

Sources & evidence

ORD record
ord-bf0e1b7dd9604ca29b4be6f68913986c
Source dataset
uspto-grants-1994_07
Patent number
US05328641

Reaction notes

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