Water → 3-(Cyclohexylmethoxy)-5-methylphenol

Temperatur

60 °C

To a solution of 5-methylbenzene-1,3-diol.H2O (1.0 g, 7.0 mmol) in DMF (15 ml) was added potassium tert-butoxide (0.86 g, 77 mmol). The mixture was stirred at 60° C. for 1 h. To the mixture was added (bromomethyl)cyclohexane (1.2 g, 7.0 mmol). The reaction mixture was stirred at 60° C. for 18 h, concentrated under vacuum, partitioned between water (40 ml) and ethyl acetate (60 ml). Ethyl acetate portion was dried over Na2SO4. Purification by chromatography (10 to 30% EtOAc-hexanes gradient) gave 3-(cyclohexylmethoxy)-5-methylphenol (133) as a light yellow solid. Yield (0.40 g, 26%): 1H NMR (400 MHz, CDCl3) δ 6.31 (s, 1H), 6.20-6.22 (m, 2H), 4.62 (bs, 1H), 3.69 (d, J=6.4 Hz, 2H), 2.50 (s, 3H), 1.64-1.88 (m, 6H), 1.16-1.34 (m, 3H), 0.98-1.08 (m, 2H).

1. stirringThe reaction mixture was stirred at 60° C. for 18 h
2. concentrationconcentrated under vacuum
3. custompartitioned between water (40 ml) and ethyl acetate (60 ml)
4. dry with materialEthyl acetate portion was dried over Na2SO4
5. customPurification by chromatography (10 to 30% EtOAc-hexanes gradient)

ORD-Eintrag

ord-81c7e6e90b6240fc8c95e26ceeb9628f

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08829244B2