3-Ethylphenol → 3-Ethyl-1-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

HRID 486421Notes

Reaction equation

[CH3:1][C:2](Cl)([CH2:4][CH2:5][C:6]([CH3:9])(Cl)[CH3:7])[CH3:3].[CH2:11]([C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1)[CH3:12].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)CCl>[CH2:11]([C:13]1[CH:18]=[C:17]2[C:16]([C:2]([CH3:3])([CH3:1])[CH2:4][CH2:5][C:6]2([CH3:9])[CH3:7])=[C:15]([OH:19])[CH:14]=1)[CH3:12]

Participants

Conditions

Temperature: 95 °C

Procedure

Next, 2,5-dimethyl-2,5-dichlorohexane (183 g, 1 mol) is stirred with 3-ethylphenol (146.4 g, 1.2 mol) and aluminum chloride (4 g) is added. The mixture is heated at 95° C., with stirring, for 1.5 hr, after which ethylene dichloride (100 ml) is added, and then the heating continued. After 1 hr, the mixture is cooled to 20° C., and poured onto an ice water/hydrochloric acid mixture (150 ml, 10% HCl solution). The mixture is then extracted with toluene (500 ml), the organic layer separated, washed with brine (3×50 ml) and dried (Na2SO4). The solvent is removed by distillation and the residue crystallized from a hexane/benzene solvent mixture to give 7-ethyl-1,1,4,4-tetramethyl-5-hydroxy-1,2,3,4-tetrahydronaphthalene.

Workup

additionis added
waitAfter 1 hr
temperaturethe mixture is cooled to 20° C.
extractionThe mixture is then extracted with toluene (500 ml)
customthe organic layer separated
washwashed with brine (3×50 ml)
dry with materialdried (Na2SO4)
customThe solvent is removed by distillation
customthe residue crystallized from a hexane/benzene solvent mixture

Sources & evidence

ORD record: ord-728eb98e0ee4493cae601ee05feae1a7
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05292719

Reaction notes

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