1-Naphthol → 1,1,1-Trifluorooctan-2-YL 2-fluoro-4-hydroxybenzoate

HRID 1728525Notes

Reaction equation

HRID 1728525 reaction equation
OC1C2C(=CC=CC=2)C=CC=1.C(OC1C=CC(C2C=CC(C([O:35][C:36]3[CH:41]=[CH:40][C:39]([C:42]([O:44][CH:45]([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:46]([F:49])([F:48])[F:47])=[O:43])=[C:38]([F:56])[CH:37]=3)=O)=CC=2)=CC=1)CCCCCCC.C(N(CC)CC)C>C(Cl)Cl>[F:56][C:38]1[CH:37]=[C:36]([OH:35])[CH:41]=[CH:40][C:39]=1[C:42]([O:44][CH:45]([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:46]([F:48])([F:49])[F:47])=[O:43]

Participants

5

Reactant 3

HCID 70051-NaphtholHCID 8471TriethylamineHCID 537499373-Fluoro-4-(1,1,1-trifluoro-2-octyloxycarbonyl)phenyl 4-octyloxybiphenyl-4'-carboxylate

Product 1

HCID 199208191,1,1-Trifluorooctan-2-YL 2-fluoro-4-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the hydroxynaphthalene (0.64 g) obtained in (2) above and triethylamine (0.3 g) in methylene chloride (40 ml) was added drop by drop the 6-(1,1,1-trifluoro-2-octyloxycarbonyl)naphthalene-2-carboxychloride (0.8 g) obtained in (1) above. To the solution was added dimethylaminopyridine (0.02 g) and the mixture was stirred at room temperature overnight. The solution was neutralized with dilute aqueous hydrochloric acid solution and extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by silica-gel column chromatography (developer: hexane/ethyl actate=20/1) to obtain the titled compound (0.4 g) having specific rotation, [α]D20 =+45.5°.

Sources & evidence

ORD record
ord-1ca1ef6aa42e4f57ad0038848d684905
Source dataset
uspto-grants-1994_07
Patent number
US05328641

Reaction notes

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