Hydrochloric Acid → HCID 17778352, compound

HRID 1954004Notes

Reaction equation

[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](O)[CH:5]=[CH:4][C:3]1=2.Cl[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24].[OH-:26].[K+].Cl>ClCCl.O.CS(C)=O>[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:18]3([N+:23]([O-:25])=[O:24])[CH:19]=[CH:20][CH:21]=[CH:22][CH:17]3[OH:26])[CH:5]=[CH:4][C:3]1=2

Participants

Conditions

Temperature: 90 °C

Procedure

DMSO (5 ml) was added to 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol (97 mg, 0.475 mmol), o-chloronitrobenzene (77 mg, 0.48 mmol) and potassium hydroxide (27 mg, 0.48 mmol), and the mixture was stirred at 90° C. for 17 hours and 30 minutes. To the reaction mixture, water, dichloromethane, and concentrated hydrochloric acid (1 ml) were added, and the organic layer was washed with diluted hydrochloric acid and brine. After dryness, the solvent was evaporated under reduced pressure to give a crude product (139.7 mg). This crude product was purified by silica gel column chromatography (AcOEt:n-hexane=1:30) to give o-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphtalenyl)-2-nitrophenol (Compound 27, 103.1 mg, 67%, colorless oil)

Workup

washthe organic layer was washed with diluted hydrochloric acid and brine
customAfter dryness, the solvent was evaporated under reduced pressure
customto give a crude product (139.7 mg)
customThis crude product was purified by silica gel column chromatography (AcOEt:n-hexane=1:30)

Sources & evidence

ORD record: ord-7408278feda04d068a552384582f3a55
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121256

Reaction notes

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