4-Decanoyloxy-2-fluorobenzoic acid → 1,1,1-Trifluoro-2-decyl 4-hydroxybenzoate

HRID 1728528

Reaction equation

HRID 1728528 reaction equation
F[C:2]1C=C(OC(CCCCCCCCC)=O)C=C[C:3]=1C(O)=O.C(OC1C=CC(C2C=CC(C([O:46][C:47]3[CH:52]=[CH:51][C:50]([C:53]([O:55][CH:56]([CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])[C:57]([F:60])([F:59])[F:58])=[O:54])=[C:49](F)[CH:48]=3)=O)=CC=2)=CC=1)CCCCCCC>O1CCCC1>[OH:46][C:47]1[CH:48]=[CH:49][C:50]([C:53]([O:55][CH:56]([CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:2][CH3:3])[C:57]([F:58])([F:59])[F:60])=[O:54])=[CH:51][CH:52]=1

Participants

4

Reactant 2

HCID 193652624-Decanoyloxy-2-fluorobenzoic acidHCID 537499373-Fluoro-4-(1,1,1-trifluoro-2-octyloxycarbonyl)phenyl 4-octyloxybiphenyl-4'-carboxylate

Product 1

HCID 147457541,1,1-Trifluoro-2-decyl 4-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the 2-fluoro-4-n-nonylcarbonyloxybenzoic acid (0.3 g) obtained in (3) above and the 1,1,1-trifluoro-2-decyl 4-hydroxybenzoate (0.3 g) obtained in (2) above in tetrahydrofuran (about 30 ml) were added dicyclohexylcarbodiimide (0.25 g) and dimethylaminopyridine (0.02 g). The solution was stirred at room temperature for about 20 hours. The solution was distilled to remove the solvent. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried over anhydrone 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 (0.21 g).

Sources & evidence

ORD record
ord-eaa54ae7bdf74895bf29218d0e8143c1
Source dataset
uspto-grants-1994_07
Patent number
US05328641

Linked notes

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