Hydroquinone → Phenoxyethyl acrylate

HRID 1440435

Reaction equation

HRID 1440435 reaction equation
[O:1]([CH2:8][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11](OC)(=[O:14])[CH:12]=[CH2:13].C[Sn](Cl)(Cl)C.C[O-].[Na+].COC1C=CC(O)=CC=1.C1(C=CC(O)=CC=1)O>CCCCCCC>[C:11]([O:10][CH2:9][CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:14])[CH:12]=[CH2:13]

Participants

8

Reactant 6

HCID 785HydroquinoneHCID 7294Methyl AcrylateHCID 90154-MethoxyphenolHCID 12955Dimethyltin dichlorideHCID 31236PhenoxyethanolHCID 10942334Sodium Methoxide

Product 1

HCID 39485Phenoxyethyl acrylateYield 91%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

In a similar manner, a mixture of 414.5 parts 2-phenoxyethanol, 388 parts methyl acrylate, 141.6 parts heptane, 4.1 parts dimethyltin dichloride, 1.1 parts sodium methoxide (molar ratio 1.09:1), 1.4 parts 4-methoxyphenol and 0.5 parts hydroquinone yielded 524.8 parts (91 percent yield, based on 2-phenoxyethanol) of 2-phenoxyethyl acrylate with a purity of 98.3 percent, containing no detectable tin.

Sources & evidence

ORD record
ord-eddedbd113144e2cb3347d25eaf899dd
Source dataset
uspto-grants-1996_03
Patent number
US05498751

Linked notes

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