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Hydroquinone → Isodecyl methacrylate

HRID 1440432
Notes
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Reaction equation

HRID 1440432 reaction equation
[CH2:1]([OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9].[C:12](OC)(=[O:16])[C:13]([CH3:15])=[CH2:14].C[Sn](Cl)(Cl)C.C[O-].[Na+].COC1C=CC(O)=CC=1.C1(C=CC(O)=CC=1)O>CCCCCCC>[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([CH3:9])[CH3:10])(=[O:16])[C:13]([CH3:15])=[CH2:14]
ParticipantsProcedureSources & evidenceReaction notes

Participants

8

Reactant 6

HCID 785HydroquinoneHCID 6658Methyl MethacrylateHCID 90154-MethoxyphenolHCID 12955Dimethyltin dichlorideHCID 32898IsodecanolHCID 10942334Sodium Methoxide

Product 1

HCID 34763
Isodecyl methacrylate
Yield 97.6%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

In a similar manner, 634.3 parts isodecyl alcohol, 603 parts methyl methacrylate, 220.6 parts heptane, 3.1 parts dimethyltin dichloride, 1.4 parts sodium methoxide (molar ratio 1.84:1) 2.21 parts 4-methoxyphenol and 0.73 parts hydroquinone were reacted as in Example 1 to yield 185.9 parts (97.6 percent yield, based on starting alcohol) of isodecyl methacrylate having a purity of 99.0 percent and containing no detectable tin.

Sources & evidence

ORD record
ord-df5ca9aca9c64748b0246b3f3da76a68
Source dataset
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05498751

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes