Naphthalene → 1,4-Dihydro-4-hydroxy-1-oxo-4-(trifluoromethyl)naphthalene

HRID 2351112Notes

Reaction equation

HRID 2351112 reaction equation
F[H-]F.[NH4+].[C:5]1(=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[CH:7]=[CH:6]1.C([Si](CC)(CC)[C:20]([F:23])([F:22])[F:21])C.C1C2C(=CC=CC=2)C=CC=1>CN(C)C=O>[OH:16][C:5]1([C:20]([F:23])([F:22])[F:21])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[CH:7]=[CH:6]1

Participants

6

Reactant 4

HCID 931NaphthaleneHCID 85301,4-NaphthoquinoneHCID 4204914Triethyl(trifluoromethyl)silaneHCID 178506426HCID 178506426, compound

Product 1

HCID 143435041,4-Dihydro-4-hydroxy-1-oxo-4-(trifluoromethyl)naphthalene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 74 mg (1.3 mmol) of ground ammonium bifluoride, 174 mg (1.1 mmol) of 1,4-naphthoquinone, and 1 mL of N,N-dimethylformamide was treated with 239 mg (1.3 mmol) of triethyltrifluoromethylsilane and stirred vigorously at room temperature for one hour. Gas chromatographic analysis of the reaction mixture showed that the major naphthalene-desired product was 1,4-dihydro-4-hydroxy-1-oxo-4-trifluoromethylnaphthalene.

Sources & evidence

ORD record
ord-1692b628dcee4bdead13930ef4a9ef9d
Source dataset
uspto-grants-1989_10
Patent number
US04871877

Reaction notes

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