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

HRID 929273Notes

Reaction equation

HRID 929273 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-71b74b57ee6c4ed9889d69f5447d6940
Source dataset
uspto-grants-2016_03
Patent number
US09293789B2

Reaction notes

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