Hydrochloric Acid → HCID 17778352, compound

HRID 1016249Notes

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-f40c2dfad0bc468589ae74ee44fd91d8
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06476017B2

Reaction notes

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