Hydroquinone → 2-Methyl-4-methylenepentanedioic acid

HRID 614674Notes

Reaction equation

HRID 614674 reaction equation
[C:1]([O:5]CC)(=[O:4])[CH:2]=[CH2:3].[C:8]([O:13]C)(=[O:12])[C:9]([CH3:11])=[CH2:10].COC.C1(C=CC(O)=CC=1)O>>[CH2:10]=[C:9]([CH2:11][CH:2]([CH3:3])[C:1]([OH:5])=[O:4])[C:8]([OH:13])=[O:12]

Participants

5

Reactant 4

HCID 785HydroquinoneHCID 6658Methyl MethacrylateHCID 8254Dimethyl EtherHCID 8821Ethyl Acrylate

Product 1

HCID 197840522-Methyl-4-methylenepentanedioic acid

Conditions

Temperature
60 °C

Procedure

Ethyl acrylate (50 g.) is added dropwise under nitrogen to a solution maintained at 60° C. and containing 500 g. of methyl methacrylate, 2.0 g. of the methyl ether of hydroquinone, and 6.0 g. of hexa-n-propylphosphorus triamide. The reaction was held at 60° C. for a total of 24 hours. After removal of unrected ethyl acrylate and methyl methacrylate, the 69.2 g. of residue analyzes for 22.4 g. of ethyl 2-methylene-4-carbomethoxypentanoate and 27.8 g. of diethyl 2-methyleneglutarate. Spectral analysis is consistent for the structure of the products. Further, hydrolysis of the ethyl 2-methylene-4-carbomethoxypentanoate gives 2-methylene-4-methylglutaric acid, which was identical to that produced in Example 1.

Workup

  1. additioncontaining 500 g
  2. customwas held at 60° C. for a total of 24 hours
  3. customAfter removal of unrected ethyl acrylate and methyl methacrylate
  4. customFurther, hydrolysis of the ethyl 2-methylene-4-carbomethoxypentanoate

Sources & evidence

ORD record
ord-0bd6b05004424a48b0a61878694a6bed
Source dataset
uspto-grants-1979_03
Patent number
US04145559

Reaction notes

Loading…