Ethylene Glycol → 5,7-Di-tert-butyl-1,4-benzodioxine

HRID 330717

반응식

HRID 330717 반응식
[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1O)[OH:8])([CH3:4])([CH3:3])[CH3:2].BrCCBr.C(=O)([O-])[O-].[K+].[K+].[CH2:27](O)[CH2:28][OH:29]>O>[C:1]([C:5]1[C:6]2[O:29][CH:28]=[CH:27][O:8][C:7]=2[CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 174Ethylene GlycolHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 755502,6-Di-tert-butylhydroquinone

생성물 1

HCID 138379325,7-Di-tert-butyl-1,4-benzodioxine

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

3,5-Di-tert-butylhydroquinone (3.33 g, 15 mmol) was combined with 1,2-dibromoethane (5.6 g), potassium carbonate (4.35 g) and ethylene glycol (25 mL). The mixture was heated in a 120° C. oil bath under an Ar atmosphere for 12 h. Water was added to the reaction mixture to quench the reaction and then the organic compound was extracted by CH2Cl2. The resulting solution was concentrated to afford a crude oil. The crude oil was then chromatographed (silica, hexane/ethyl acetate=20:1) mixture to afford the title compound (Rf=0.5, 5:1 hexane/ethyl acetate). 1H NMR (500 MHz, CDCl3): δ 7.03 (d, J=2 Hz, 1H), 6.93 (d, J=2 Hz, 1H), 4.34 (s, 4H), 1.53 (s, 9H), 1.43 (s, 9H).

후처리

  1. customto quench
  2. customthe reaction
  3. extractionthe organic compound was extracted by CH2Cl2
  4. concentrationThe resulting solution was concentrated
  5. customto afford a crude oil
  6. customThe crude oil was then chromatographed (silica, hexane/ethyl acetate=20:1) mixture

출처 및 근거

ORD 기록
ord-c247f44ca28e4ae882317b74efb8bdc6
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877390B2

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