Hydroquinone → (-)-p-(2-Cyano-2-methylhexyloxy)phenol

HRID 1461200Notes

Reaction equation

C1(C)C=CC(S(O[CH2:11][C:12]([C:18]#[N:19])([CH3:17])[CH2:13][CH2:14][CH2:15][CH3:16])(=O)=O)=CC=1.[C:21]1([CH:28]=[CH:27][C:25]([OH:26])=[CH:24][CH:23]=1)[OH:22].[O-]CCCC.[Na+].[OH-].[Na+].[Cl-].[Na+]>C(O)CCC>[C:18]([C:12]([CH3:17])([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:11][O:22][C:21]1[CH:28]=[CH:27][C:25]([OH:26])=[CH:24][CH:23]=1)#[N:19]

Participants

Conditions

Temperature: 120 °C

Procedure

While 480 mg (1.6 mM) of (+) 2-cyano-2-methylhexyl p-toluenesulfonate, 357 mg (3.2 mM) of hydroquinone and 1.5 ml of n-butanol were stirred in a nitrogen atmosphere, sodium butoxide obtained by dissolving 83.3 mM (2.1 mM) of sodium hydroxide in 2.2 ml of n-butanol was added dropwise, followed by stirring for 20 hours under heating at 120° C. After the reaction, 5 ml of saturated sodium chloride aqueous solution was added, followed by extraction with ether. The ether layer was washed with distilled water and dried on sodium sulfate, followed by distilling-off of the solvent to obtain 296 mg of a crude product, which was then purified by thine layer chromatography (developer solvent: methylene chloride) to obtain 81.3 mg of (-)-p-(2-cyano-2-methylhexyloxy)phenol (Yield: 19.1%). [α]D -1.8 degree (c 0.836, benzene).

Workup

customobtained
additionwas added dropwise
additionwas added
extractionfollowed by extraction with ether
washThe ether layer was washed with distilled water
customdried on sodium sulfate
customto obtain 296 mg of a crude product, which
customwas then purified by thine layer chromatography (developer solvent: methylene chloride)

Sources & evidence

ORD record: ord-af58d263978c43d4bd8e72a5f4f5c970
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075031

Reaction notes

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