Chloride → 2-Methyladamantan-2-yl Acrylate (stabilized with MEHQ)

HRID 1699133Notes

Reaction equation

HRID 1699133 reaction equation
[CH3:1][C:2]1([OH:12])[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.[C:13](Cl)(=[O:16])[CH:14]=[CH2:15].CO.[Cl-]>C(C(C)=O)C.O.C(N(CC)CC)C>[C:13]([O:12][C:2]1([CH3:1])[CH:3]2[CH2:11][CH:7]3[CH2:6][CH:5]([CH2:10][CH:9]1[CH2:8]3)[CH2:4]2)(=[O:16])[CH:14]=[CH2:15]

Participants

8

Reactant 4

HCID 312ChlorideHCID 887MethanolHCID 13140Acryloyl chlorideHCID 1365452-Methyl-2-adamantanol

Product 1

HCID 112182922-Methyladamantan-2-yl Acrylate (stabilized with MEHQ)Yield 98.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Into a reaction vessel were charges 33.26 g of methyl ethyl ketone, 16.63 g (0.1 mol) of 2-methyl-2-adamantanol and 30.36 (0.3 mol) of triethylamine, and their temperature was elevated to 60° C. under stirring. To the mixture, a solution prepared by dissolving 13.58 g (0.15 mol) of acryloyl chloride in 16.63 g of methyl ethyl ketone was added dropwise. At the end of dropwise addition, the temperature was reached 77° C. and the mixture was boiling with the reaction heat. The mixture was kept in a boiling state for 3 hours with stirring to complete the reaction. After cooling, 3.20 g (0.1 mol) of methanol was added dropwise to deactivate the unreacted acryloly chloride while keeping the temperature below 40° C. Then, 103 g of water was added to wash the mixture and thereafter the mixture was separated into layers. To the brown organic layer, 10 g of active carbon (Carborafin) was added and stirred. The mixture was thereafter filtered and the residue was washed with methyl ethyl ketone. The filtrate and washing effluents were combined and concentrated at a bath temperature of 45° C. to obtain 21.68 g of reddish orange crude 2-methyl-2-adamantyl acrylate.

Workup

  1. customInto a reaction vessel were
  2. customwas elevated to 60° C.
  3. customTo the mixture, a solution prepared
  4. additionwas added dropwise
  5. additionAt the end of dropwise addition
  6. customwas reached 77° C.
  7. temperatureheat
  8. stirringwith stirring
  9. customthe reaction
  10. temperatureAfter cooling
  11. customthe temperature below 40° C
  12. washto wash the mixture
  13. customthe mixture was separated into layers
  14. additionTo the brown organic layer, 10 g of active carbon (Carborafin) was added
  15. stirringstirred
  16. filtrationThe mixture was thereafter filtered
  17. washthe residue was washed with methyl ethyl ketone
  18. washThe filtrate and washing effluents
  19. concentrationconcentrated at a bath temperature of 45° C.

Sources & evidence

ORD record
ord-fea678a7b2c94852883a21c88ca7daa2
Source dataset
uspto-grants-2002_02
Patent number
US06344582B1

Reaction notes

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