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

HRID 1085350Notes

Reaction equation

HRID 1085350 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>>[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

5

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

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-dimethylformam:ide 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-d937efd2e2da45f29e86de7224791578
Source dataset
uspto-grants-1991_04
Patent number
US05008425

Reaction notes

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