Methacrylic Acid → 2-Propenoic acid, 2-methyl-, (tricyclo[3.3.1.13,7]dec-2-yloxy)methyl ester

HRID 1716170Notes

Reaction equation

HRID 1716170 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].C(N(CC)CC)C.Cl[CH2:15][O:16][CH:17]1[CH:24]2[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:26][CH:18]1[CH2:19]3)[CH2:23]2>O1CCCC1>[CH:18]12[CH2:26][CH:22]3[CH2:21][CH:20]([CH2:25][CH:24]([CH2:23]3)[CH:17]1[O:16][CH2:15][O:5][C:1](=[O:6])[C:2]([CH3:4])=[CH2:3])[CH2:19]2

Participants

5

Reactant 3

HCID 4093Methacrylic AcidHCID 8471TriethylamineHCID 10932491HCID 10932491, compound

Product 1

HCID 231508582-Propenoic acid, 2-methyl-, (tricyclo[3.3.1.13,7]dec-2-yloxy)methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6.9 g of methacrylic acid was dissolved in 200 ml of tetrahydrofuran, and 8.0 g of triethylamine was added. Following stirring at room temperature, a solution containing 15 g of 2-adamantyl chloromethyl ether dissolved in 100 ml of tetrahydrofuran was added dropwise to the reaction solution. Following stirring for 12 hours at room temperature, the precipitated salt was removed by filtration. The solvent was removed from the remaining filtrate by evaporation, the residue was dissolved in 200 ml of ethyl acetate, and following washing with pure water (100 ml×3), the solvent was removed by evaporation. The residue was then allowed to stand under ice cooling, thereby yielding a white solid.

Workup

  1. additionwas added dropwise to the reaction solution
  2. stirringFollowing stirring for 12 hours at room temperature
  3. customthe precipitated salt was removed by filtration
  4. customThe solvent was removed from the remaining filtrate by evaporation
  5. dissolutionthe residue was dissolved in 200 ml of ethyl acetate
  6. washfollowing washing with pure water (100 ml×3)
  7. customthe solvent was removed by evaporation
  8. customyielding a white solid

Sources & evidence

ORD record
ord-5c70ff849142413b982041e4b5459fee
Source dataset
uspto-grants-2010_09
Patent number
US07803512B2

Reaction notes

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