Methacrylic Acid → Oxolan-2-yl 2-methylprop-2-enoate

HRID 459063Notes

Reaction equation

HRID 459063 reaction equation
ClCCl.[C:4]([OH:9])(=[O:8])[C:5]([CH3:7])=[CH2:6].[O:10]1[CH:14]=[CH:13][CH2:12][CH2:11]1>CS(O)(=O)=O.C(N(CC)CC)C>[C:4]([O:9][CH:11]1[CH2:12][CH2:13][CH2:14][O:10]1)(=[O:8])[C:5]([CH3:7])=[CH2:6]

Participants

6

Reactant 3

HCID 4093Methacrylic AcidHCID 6344DichloromethaneHCID 709342,3-Dihydrofuran

Product 1

HCID 154299Oxolan-2-yl 2-methylprop-2-enoateYield 58%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
-40 °C

Procedure

To a 500-mL, 3-necked round bottomed flask equipped with a thermocouple temperature monitor, nitrogen inlet and a magnetic stirrer was added 300 mL of dichloromethane, 24.5 g (0.29 mol) of methacrylic acid and 21.4 g (0.305 mol) of 2,3-dihydrofuran. The flask was cooled under Nitrogen to −40° C. and 0.05 g of methanesulfonic acid was added. The mixture was warmed to 0° C. and stirred for 6 hours at which time it was recooled to −40° C. and an excess (1 mL) of triethylamine was added. The solution was then washed with saturated sodium bicarbonate, water and brine and dried over anhydrous magnesium sulfate. Distillation from sodium carbonate at reduced pressure resulted in 26 g (58%) of the title compound.

Workup

  1. customTo a 500-mL, 3-necked round bottomed flask equipped with a thermocouple temperature monitor, nitrogen inlet and a magnetic stirrer
  2. temperatureThe mixture was warmed to 0° C.
  3. customwas recooled to −40° C.
  4. washThe solution was then washed with saturated sodium bicarbonate, water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationDistillation from sodium carbonate at reduced pressure

Sources & evidence

ORD record
ord-7bc2e074d52a4aa695f8f7e42d92b1d6
Source dataset
uspto-grants-2007_03
Patent number
US07193023B2

Reaction notes

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