Methacrylic Acid → (3-Formyl-4-hydroxyphenyl)methyl 2-methylprop-2-enoate

HRID 615645Notes

Reaction equation

HRID 615645 reaction equation
Cl[CH2:2][C:3]1[CH:10]=[C:7]([CH:8]=[O:9])[C:6]([OH:11])=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+].[C:17]([OH:22])(=[O:21])[C:18]([CH3:20])=[CH2:19]>CC(C)=O>[C:17]([O:22][CH2:2][C:3]1[CH:10]=[C:7]([CH:8]=[O:9])[C:6]([OH:11])=[CH:5][CH:4]=1)(=[O:21])[C:18]([CH3:20])=[CH2:19]

Participants

5

Reactant 3

HCID 4093Methacrylic AcidHCID 3352915-(Chloromethyl)-2-hydroxybenzaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 20095941(3-Formyl-4-hydroxyphenyl)methyl 2-methylprop-2-enoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Chloromethylsalicylaldehyde (34 g) (prepared by the method of Angyal et al., J. Chem. Soc. 2141, (1950)) was added to a stirred mixture of acetone (250 ml), sodium hydrogen carbonate (33.6 g), and methacrylic acid (34.4 g) and the mixture was stirred under reflux for 21/2 hours. Addition of the mixture to ice water gave a grey precipitate which was collected, washed with water, dried, and crystallized from light petroleum (b.p. 60°-80° C.). Yield 32.1 g, m.p. 82-4.

Workup

  1. temperatureunder reflux for 21/2 hours
  2. customgave a grey precipitate which
  3. customwas collected
  4. washwashed with water
  5. customdried
  6. customcrystallized from light petroleum (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-5f72cffaa1e14496a683de0fc4a13ae8
Source dataset
uspto-grants-1985_02
Patent number
US04500601

Reaction notes

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