Hydroquinone → Decyl methacrylate

HRID 538963

Reaction equation

HRID 538963 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:8](O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]C.[Li+].[Cl-].C1C2NC3C(=CC=CC=3)SC=2C=CC=1.C1(C=CC(O)=CC=1)O>C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Zn+2].CO>[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

8

Reactant 5

HCID 785HydroquinoneHCID 6658Methyl Methacrylate2×HCID 7108PhenothiazineHCID 81741-DecanolHCID 433294Lithium Chloride

Product 1

HCID 18510Decyl methacrylateYield 99.1%

Reagents, catalysts & solvents 2

HCID 5360437zinc;(Z)-4-oxopent-2-en-2-olateCatalystHCID 887MethanolSolvent

Procedure

To a 1 liter flask equipped with an agitator, thermometer and a Vigreux fractionating column were added 188 g (1.88 mol) of methyl methacrylate (MMA), 59.4 g (0.376 mol) of n-decyl alcohol, 1.25 mol % of zinc acetylacetonate, 1.25 mol % of LiCl and 0.75 g of phenothiazine, and 0.62 g of hydroquinone free radical polymerization inhibitor. The mixture was heated to reflux at atmospheric pressure while an azeotropic mixture of MMA and methanol was removed from the upper part of the fractionation column. The reaction was continued in this manner for approximately five hours. After vacuum filtration of the catalyst and inhibitors, the excess of MMA was removed under vacuum and the resulting n-decyl methacrylate (DMA) was isolated (84.3 grams, 99.1% yield) and analyzed. Gas-liquid chromatographic (GLC) analysis showed 99% conversion of 1-decanol to DMA of 98% purity.

Workup

  1. customTo a 1 liter flask equipped with an agitator
  2. temperatureThe mixture was heated
  3. customwas removed from the upper part of the fractionation column
  4. filtrationAfter vacuum filtration of the catalyst and inhibitors
  5. customthe excess of MMA was removed under vacuum

Sources & evidence

ORD record
ord-9b6b581d4a754dddad895a3cb06d7e05
Source dataset
uspto-grants-2014_10
Patent number
US08865931B2

Linked notes

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