Toluene → 1-Adamantyl methacrylate

HRID 982909Notes

Reaction equation

HRID 982909 reaction equation
C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:19]12([OH:29])[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2.[C:30](O)(=[O:34])[C:31]([CH3:33])=[CH2:32]>O>[C:30]([O:29][C:19]12[CH2:26][CH:25]3[CH2:24][CH:23]([CH2:22][CH:21]([CH2:27]3)[CH2:20]1)[CH2:28]2)(=[O:34])[C:31]([CH3:33])=[CH2:32]

Participants

6

Reactant 4

HCID 1140TolueneHCID 4093Methacrylic AcidHCID 6101p-Toluenesulfonic acidHCID 641521-Adamantanol

Product 1

HCID 109550921-Adamantyl methacrylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

200 ml of toluene and 1 g of p-toluenesulfonic acid were added to 70 g of 1-adamantanol and 50 g of methacrylic acid. They were subjected to a reaction with heating and stirring, while water was distilled off using a Dean-Stark trap. The resulting organic phase was washed with water, a 10 mass % aqueous sodium hydrogencarbonate solution and water in this order and distilled to obtain crude 1-adamantyl methacrylate (a crude product) having a purity of 91 mass %.

Workup

  1. customThey were subjected to a reaction
  2. temperaturewith heating
  3. distillationwas distilled off
  4. washThe resulting organic phase was washed with water
  5. distillationa 10 mass % aqueous sodium hydrogencarbonate solution and water in this order and distilled

Sources & evidence

ORD record
ord-e93d113b6c164b0cb5257a0ce2200bbc
Source dataset
uspto-grants-2005_03
Patent number
US06861552B2

Reaction notes

Loading…