Benzene → 2-Methylbut-3-yn-2-yl 2-methylprop-2-enoate

HRID 1109608Notes

Reaction equation

HRID 1109608 reaction equation
C1C=CC=CC=1.[CH3:7][C:8]([OH:12])([C:10]#[CH:11])[CH3:9].[CH3:13][C:14]([C:16](Cl)=[O:17])=[CH2:15]>N1C=CC=CC=1>[C:16]([O:12][C:8]([CH3:9])([C:10]#[CH:11])[CH3:7])(=[O:17])[C:14]([CH3:15])=[CH2:13]

Participants

5

Reactant 3

HCID 241BenzeneHCID 82582-Methyl-3-butyn-2-olHCID 13528Methacryloyl chloride

Product 1

HCID 145920562-Methylbut-3-yn-2-yl 2-methylprop-2-enoateYield 62%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A reactor was charged with 550 parts of benzene, 74 parts of pyridine and 65.5 parts of 2-methyl-3-butyn-2-ol. To this were added 90 parts of methacryl chloride dropwise over one hour while keeping the inner temperature at 20° C. Then the reaction mixture was kept at 50° C. for 6 hours, suction filtered, evaporated and distilled in vacuo. 2-Methyl-3-butyn-2-yl methacrylate boiling at 56°-58° C./12 mmHg was obtained in a yield of 62% of theory. The product was identified by the IR spectrum thereof.

Workup

  1. customat 20° C
  2. filtrationsuction filtered
  3. customevaporated
  4. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-47d44221a77f460ba6252037df8bfaf9
Source dataset
uspto-grants-1994_06
Patent number
US05321082

Reaction notes

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