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

HRID 330717

反応式

HRID 330717 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c247f44ca28e4ae882317b74efb8bdc6
出典データセット
uspto-grants-2014_11
特許番号
US08877390B2

関連ノート

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