Methacrylic Acid → 2-Propynyl methacrylate

HRID 743415Notes

Reaction equation

HRID 743415 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:7](O)[C:8]#[CH:9].C(C1C=C(O)C(=CC=1)O)(C)(C)C>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>[C:1]([O:6][CH2:9][C:8]#[CH:7])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 3

HCID 4093Methacrylic AcidHCID 73814-tert-ButylcatecholHCID 7859Propargyl alcohol

Product 1

HCID 837782-Propynyl methacrylateYield 75%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A solution of 86 g. (1 mole) of methacrylic acid in 120 ml. benzene was reacted with 67.2 g. (1.2 moles) of propargyl alcohol in the presence of 4 g. of p-toluenesulfonic acid as a catalyst and 0.4 g. p-tertbutylcatechol as an inhibitor. The reaction mixture was stirred and heated to reflux under nitrogen until 18 g. of water was azeotroped over into a Dean-Stark trap. The reaction mixture was neutralized with saturated sodium carbonate aqueous solution, washed with deionized water three times and dried over sodium carbonate. The solvent was removed on a Rotavapor. Vacuum distillation of the residue in the presence of the inhibitor gave a 75% yield of propargyl methacrylate obtained as a clear colorless liquid.

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen until 18 g
  3. customof water was azeotroped over into a Dean-Stark trap
  4. washwashed with deionized water three times
  5. dry with materialdried over sodium carbonate
  6. customThe solvent was removed on a Rotavapor
  7. distillationVacuum distillation of the residue in the presence of the inhibitor

Sources & evidence

ORD record
ord-2c785e3aa5554722a32de6e26a7d2a35
Source dataset
uspto-grants-1996_09
Patent number
US05556921

Reaction notes

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