Hydroquinone → HCID 14401402, compound

HRID 340816Notes

Reaction equation

HRID 340816 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].C1(C=CC(O)=CC=1)O.[CH:15](O)=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CC1C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>[C:1]([O:6][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=[CH2:15])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 3

HCID 785HydroquinoneHCID 4093Methacrylic AcidHCID 44135745Undec-1-en-1-ol

Product 1

HCID 14401402HCID 14401402, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

Monomer synthesis. In a 3 neck round bottom flask, methacrylic acid (51.4 g, 0.515 mol) and benzene (60 ml) were combined. P-TSA (0.90 g, 2.6 mmol), hydroquinone (1.56 g, 13.6 mmol) and undecene-1-ol (25.8 g, 0.150 mol) were added into the flask and a Dean Stark adapter was attached. The reaction was heated at reflux overnight. The benzene was removed from the solution by rotary evaporation at reduced pressure and ether (200 ml) was added. NaHCO3 (50 g) was added to the ether solution to remove any excess methacrylic acid. The product was decanted from the NaHCO3 and washed with H2O (200 ml) 3 times, with 5% by weight NaHCO3 (200 ml) solution 3 times, and again with H2O (200 ml) 3 times. The product was dried over MgSO4 and the ether was removed by rotary evaporation. The product was distilled at 110° C. at 150 mTorr to yield 18.3 g (51% yield) of undec-10-enyl methacrylate.

Workup

  1. customMonomer synthesis
  2. temperatureThe reaction was heated
  3. temperatureat reflux overnight
  4. customThe benzene was removed from the solution by rotary evaporation at reduced pressure and ether (200 ml)
  5. additionwas added
  6. additionNaHCO3 (50 g) was added to the ether solution
  7. customto remove any excess methacrylic acid
  8. customThe product was decanted from the NaHCO3
  9. washwashed with H2O (200 ml) 3 times, with 5% by weight NaHCO3 (200 ml) solution 3 times
  10. dry with materialThe product was dried over MgSO4
  11. customthe ether was removed by rotary evaporation
  12. distillationThe product was distilled at 110° C. at 150 mTorr

Sources & evidence

ORD record
ord-8ceec9c534694023b63de58622db08e0
Source dataset
uspto-grants-2014_11
Patent number
US08895667B2

Reaction notes

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