Methacrylic Acid → Triphenylmethyl 2-methylprop-2-enoate

HRID 978966Notes

Reaction equation

HRID 978966 reaction equation
C(N(CC)CC)C.[H-].[Ca+2].[H-].[C:11]([OH:16])(=[O:15])[C:12]([CH3:14])=[CH2:13].[C:17]1([C:23](Br)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCOCC>[C:11]([O:16][C:23]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)(=[O:15])[C:12]([CH3:14])=[CH2:13]

Participants

6

Reactant 4

HCID 4093Methacrylic AcidHCID 8471TriethylamineHCID 11692BromotriphenylmethaneHCID 3033859Calcium hydride

Product 1

HCID 12641353Triphenylmethyl 2-methylprop-2-enoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

5.05 g (0.05 mol) of dry triethylamine distilled in the presence of calcium hydride was added to 20 ml of anhydrous ether distilled in the presence of lithium aluminum hydride, and the mixture was cooled with ice in a nitrogen atmosphere. 0.86 g (0.01 mol) of methacrylic acid was added thereto and the mixture was stirred. While cooling the mixture with ice, 3.23 g (0.01 mol) of triphenylmethyl bromide dissolved in 10 ml of anhydrous ether was added thereto, whereby the reaction rapidly proceeded and triethylamine hydrobromide was precipitated. The reaction was continued for 2.5 hr until the salt was completely precipitated, and the resulting crystal was recovered by filtration. When the solvent and excess triethylamine were distilled off, triphenylmethyl methacrylate was obtained as a crystal, which was then recrystallized from ether to give 3.07 g (yield: 92.9%) of a colorless prismatic crystal.

Workup

  1. distillationdistilled in the presence of lithium aluminum hydride
  2. temperaturethe mixture was cooled with ice in a nitrogen atmosphere
  3. additionwas added
  4. customwhereby the reaction
  5. customtriethylamine hydrobromide was precipitated
  6. customwas completely precipitated
  7. filtrationthe resulting crystal was recovered by filtration
  8. distillationWhen the solvent and excess triethylamine were distilled off

Sources & evidence

ORD record
ord-2c8d2afca6924888b239cc86cfec1d8d
Source dataset
uspto-grants-1987_05
Patent number
US04666633

Reaction notes

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