Methanesulfonic Acid → Octyl acrylate

HRID 513884

Reaction equation

HRID 513884 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:9]([OH:13])(=[O:12])[CH:10]=[CH2:11].CS(O)(=O)=O.COC1C=CC(O)=CC=1>O.O.[Cu](Cl)Cl>[C:9]([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])(=[O:12])[CH:10]=[CH2:11]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 6581Acrylic AcidHCID 81251-OcteneHCID 90154-Methoxyphenol

Product 1

HCID 17258Octyl acrylate

Reagents, catalysts & solvents 1

HCID 61482Cupric chloride dihydrateCatalyst

Conditions

Temperature
105 °C

Procedure

A mixture of 15.0 g (134 mmoles, 3 eq) of 1-octene, 3.21 g (44.6 mmoles, 1 eq) of acrylic acid, 0.257 g (2.67 mmoles, 0.06 eq) of methanesulfonic acid, 0.0277 g of MEHQ and 0.0034 g of copper(II) chloride dihydrate was heated at 105° C. for 22 hours to give 2.5% conversion to octyl acrylate based on acrylic acid consumed.

Sources & evidence

ORD record
ord-5a70f24bd13042c58ae2ec49962b0a4a
Source dataset
uspto-grants-2015_08
Patent number
US09102774B2

Linked notes

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