Hydroquinone → HCID 53959473, compound

HRID 2406902Notes

Reaction equation

HRID 2406902 reaction equation
[C:1]([O:6][CH2:7][C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])(=[O:5])[C:2]([CH3:4])=[CH2:3].C1(C=CC(O)=CC=1)O.[CH2:21]=[C:22]1[O:26][C:24](=[O:25])[CH2:23]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[O:26]=[C:22]([CH3:21])[CH2:23][C:24]([O:10][CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7][O:6][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])=[O:25]

Participants

6

Reactant 3

HCID 785HydroquinoneHCID 12661Diketene2×HCID 834923-Hydroxy-2,2-dimethylpropyl methacrylate

Product 1

HCID 53959473HCID 53959473, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

To a 2-L flask was charged neopentyl glycol (208.3 g, 2.0 moles), toluene (250 mL), hydroquinone (0.5 g) and sodium methoxide (25% in methanol, 8 g). The mixture was heated to 60-65° C. and methyl methacrylate (120 g, 1.2 moles) was added dropwise over 1 hour. The reaction was held at 70° C. for one hour under moderate vacuum to remove methanol and low boilers. Reaction was worked up by washing with 2×250 mL water and 1×100 mL saturated sodium chloride solution at 70° C. Toluene was evaporated and the resulting crude product (166 g) distilled to provide 3-hydroxy-2,2-dimethylpropyl methacrylate of 97% GC assay. To a 300 mL flask was charged 3-hydroxy-2,2-dimethylpropyl methacrylate (11.5 g, 0.064 moles), methylene chloride (20 g), DMAP (0.01 g), hydroquinone (0.05 g) and the mixture cooled to 0-5° C. To this was added dropwise diketene (5.4 g) at <3° C. Reaction allowed to warm to room temperature and stir overnight. Reaction cooled to 0-5° C. and additional diketene (2 g) added to complete reaction. Once reaction was complete, the dichloromethane was removed at 60° C. with house vacuum. Crude product distilled via Kugelrohr distillation to provide desired product of 92.6% assay with 1.6% starting material remaining (GC assay).

Workup

  1. customReaction
  2. temperatureto warm to room temperature
  3. customReaction
  4. temperaturecooled to 0-5° C.
  5. customOnce reaction
  6. customthe dichloromethane was removed at 60° C. with house vacuum
  7. distillationCrude product distilled via Kugelrohr distillation

Sources & evidence

ORD record
ord-5d5a4770e06f4258a08a702451dcc868
Source dataset
uspto-grants-2014_08
Patent number
US08809447B2

Reaction notes

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