Hydroquinone → HCID 68637785, compound

HRID 1033260Notes

Reaction equation

HRID 1033260 reaction equation
[C:1]1([CH:8]=[CH:7][C:5](O)=[CH:4][CH:3]=1)O.[C:9]([OH:14])(=[O:13])[C:10]([CH3:12])=[CH2:11].O1CCCC1.P(Cl)(Cl)(Cl)=O>CO.C(N(CC)CC)C.C1(C)C=CC=CC=1>[C:9]([OH:14])(=[O:13])[C:10]([CH3:12])=[CH2:11].[C:9]([OH:14])(=[O:13])[C:10]([CH3:12])=[CH2:11].[CH:1]1[CH:8]=[CH:7][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 785HydroquinoneHCID 4093Methacrylic AcidHCID 8028TetrahydrofuranHCID 24813Phosphorus oxychloride

Product 1

HCID 68637785HCID 68637785, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

Into a one liter three neck flask which was equipped with a stirrer, water condenser, thermometer and addition funnel was added 55g hydroquinone (1,4-benzenediol), 94.5g methacrylic acid (MAA), 100 ml tetrahydrofuran and 350ml toluene. Then 244 g of triethylamine was added with cooling. Then 121 g phosphorus oxychloride (POCl3) was added over a 20 minute period between 22° and 55° C. The flask contents were further reacted at 72° C. for two hours and then filtered. The filtrate was distilled to remove the volatiles, thus leaving 75 g of an amber crystalline semi solid. It was dissolved in 250 ml of methanol and crystallized in dry ice to give a white powder with a melting point of 87° to 89° C. Gel Permeation Chromatography (GPC) and NMR confirmed that the product was the 1,4-benzene dimethacrylate.

Workup

  1. additionthermometer and addition funnel
  2. temperaturewith cooling
  3. customThe flask contents were further reacted at 72° C. for two hours
  4. filtrationfiltered
  5. distillationThe filtrate was distilled
  6. customto remove the volatiles
  7. customthus leaving 75 g of an amber crystalline semi solid
  8. customcrystallized in dry ice
  9. customto give a white powder with a melting point of 87° to 89° C

Sources & evidence

ORD record
ord-5f2b031aaf254ee690837ad75ef03b26
Source dataset
uspto-grants-1994_05
Patent number
US05310811

Reaction notes

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