Hydroquinone → Isooctyl acrylate

HRID 1440433Notes

Reaction equation

HRID 1440433 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].[C:10](OC)(=[O:13])[CH:11]=[CH2:12].C[Sn](Cl)(Cl)C.[OH-].[Na+].COC1C=CC(O)=CC=1.C1(C=CC(O)=CC=1)O>CCCCCCC>[C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7])(=[O:13])[CH:11]=[CH2:12]

Participants

8

Reactant 6

HCID 785HydroquinoneHCID 7294Methyl AcrylateHCID 90154-MethoxyphenolHCID 12955Dimethyltin dichlorideHCID 14798Sodium HydroxideHCID 15450Isooctan-1-ol

Product 1

HCID 165746Isooctyl acrylateYield 97%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

In a similar manner, a mixture of 520.9 parts isooctyl alcohol, 516.6 parts methyl acrylate, 183 parts heptane, 2.4 parts dimethyltin dichloride, 0.5 parts sodium hydroxide (molar ratio 1.14:1), 1.6 parts 4-methoxyphenol and 0.6 parts hydroquinone yielded, after reaction and work up as in Example 1, 715.2 parts (97 percent yield, based on isooctyl alcohol) of isooctyl acrylate with a purity of 99.9 percent, containing no detectable tin.

Workup

  1. customyielded
  2. customafter reaction

Sources & evidence

ORD record
ord-8d3d74aefb4f461da25dcb99accfcf27
Source dataset
uspto-grants-1996_03
Patent number
US05498751

Reaction notes

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