Potassium Carbonate → (3-((8-(1,3-Dioxolan-2-yl)octyl)oxy)-4-methylphenyl)methanol

HRID 332663노트

반응식

HRID 332663 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:10])=[C:7]([OH:9])[CH:8]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]1[O:24][CH2:23][CH2:22][O:21]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[O:21]1[CH2:22][CH2:23][O:24][CH:20]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:9][C:7]1[CH:8]=[C:3]([CH2:2][OH:1])[CH:4]=[CH:5][C:6]=1[CH3:10]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 115210855-(Hydroxymethyl)-2-methylphenolHCID 118323182-(8-Bromooctyl)-1,3-dioxolane

생성물 1

HCID 71093153(3-((8-(1,3-Dioxolan-2-yl)octyl)oxy)-4-methylphenyl)methanol수율 41.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a stirred solution of 5-(hydroxymethyl)-2-methylphenol (0.57 g, 4.15 mmol) in dimethyl formamide (15 mL), was added 2-(8-bromooctyl)-1,3-dioxolane (1.00 g, 3.77 mmol) and potassium carbonate (0.63 g, 4.57 mmol), and the mixture was stirred at 80° C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried (magnesium sulphate), filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-7% ethyl acetate in iso-hexane to afford the title compound (0.5 g, 41%).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with 0-7% ethyl acetate in iso-hexane

출처 및 근거

ORD 기록
ord-2a390853a79644c2b21b48501b8ef6c7
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877774B2

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