Water → 3-(Cyclohexylmethoxy)-5-methylphenol

HRID 74408

반응식

HRID 74408 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([OH:8])[CH:7]=1.O.CC(C)([O-])C.[K+].Br[CH2:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C=O)C>[CH:19]1([CH2:18][O:8][C:6]2[CH:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[CH:7]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

참가 물질

6

반응물 4

HCID 962WaterHCID 10436OrcinolHCID 137636Cyclohexane, (bromomethyl)-HCID 23665647Potassium tert-butoxide

생성물 1

HCID 230943513-(Cyclohexylmethoxy)-5-methylphenol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-81c7e6e90b6240fc8c95e26ceeb9628f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829244B2

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