Water → 2-Methyl-2-adamantyl methacrylate

HRID 1837323Notes

Reaction equation

HRID 1837323 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[O:11])[CH2:8]2.[CH3:12][Mg]Br.[C:15](Cl)(=[O:19])[C:16]([CH3:18])=[CH2:17].O>O1CCCC1.C(N(CC)CC)C.C(O)COCCO>[C:15]([O:11][C:2]1([CH3:12])[CH:3]2[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][CH:1]1[CH2:8]3)[CH2:4]2)(=[O:19])[C:16]([CH3:18])=[CH2:17]

Participants

8

Reactant 4

HCID 962WaterHCID 13528Methacryloyl chlorideHCID 64151AdamantanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 98375662-Methyl-2-adamantyl methacrylateYield 51%

Reagents, catalysts & solvents 3

HCID 8117Diethylene GlycolCatalystHCID 8471TriethylamineCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

15 g (0.1 mol) of 2-adamantanone obtained in Example 1 was dissolved in 50 ml of tetrahydrofuran, and 100 ml (1 mol/l) of a tetrahydrofuran solution of methyl magnesium bromide prepared in advance was added dropwise to the above solution at 40° C. or less. After the proceeding of a reaction was checked by gas chromatography, 2.5 g (0.025 mol) of triethylamine and 13 g (0.125 mol) of methacrylic acid chloride were added to the reaction solution and stirred at 50° C. for 3 hours. The proceeding of the reaction was checked by gas chromatography, and then 10 ml of water was added to stop the reaction. Thereafter, tetrahydrofuran was distilled off under reduced pressure, 50 ml of heptane was added, and the obtained solid was washed with a 1N aqueous solution of ammonium chloride, a 10% aqueous solution of sodium hydroxide and ion exchange water sequentially. Thereafter, heptane was distilled off in reduced pressure to obtain 24 g of a crude product. When 1.5 g of diethylene glycol was added to this crude product to carry out vacuum distillation (92° C./0.4 mmHg), 12 g (0.51 mol, 51%) of 2-methyl-2-adamantyl methacrylate was obtained.

Workup

  1. additionwas added dropwise to the above solution at 40° C. or less
  2. additionwere added to the reaction solution
  3. customthe reaction
  4. distillationThereafter, tetrahydrofuran was distilled off under reduced pressure, 50 ml of heptane
  5. additionwas added
  6. washthe obtained solid was washed with a 1N aqueous solution of ammonium chloride
  7. distillationThereafter, heptane was distilled off in reduced pressure
  8. customto obtain 24 g of a crude product
  9. distillationvacuum distillation (92° C./0.4 mmHg)

Sources & evidence

ORD record
ord-3cd2945b48184d209f8713b7ced434e1
Source dataset
uspto-grants-2004_08
Patent number
US06781016B2

Reaction notes

Loading…