Methacryloyl chloride → 2-Propenoic acid, 4-benzoylphenyl ester

HRID 1055355Notes

Reaction equation

HRID 1055355 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:17]=[CH:16][C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:6][CH:5]=1.[C:18](Cl)(=[O:22])[C:19](C)=[CH2:20]>C(C(C)=O)C>[C:18]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:16][CH:17]=1)(=[O:22])[CH:19]=[CH2:20]

Participants

5

Reactant 3

HCID 13528Methacryloyl chlorideHCID 143474-HydroxybenzophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 30151312-Propenoic acid, 4-benzoylphenyl esterYield 71.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

1.3 g (16.25 mmoli) of NaOH 50% water solution, were added to a solution of 3 g (15.21 mmol) of 4-hydroxybenzophenone in 20 cc of methyl ethyl ketone. After 30 minutes under stirring, a solution of 1.59 g (15.21 mmol) of methacryloyl chloride in 5 mL of methyl ethyl ketone were added dropwise. After the addition the reaction mixture was stirred for 1 hour, filtered and the solvent was evaporated. The oil residue was purified by flash chromatography on silica gel (eluent CH2Cl2) to obtain 2.74 g of a colourless liquid.

Workup

  1. additionAfter the addition the reaction mixture
  2. stirringwas stirred for 1 hour
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe oil residue was purified by flash chromatography on silica gel (eluent CH2Cl2)

Sources & evidence

ORD record
ord-35e8a8427f89447fa3b1cf2fba54773f
Source dataset
uspto-grants-2016_07
Patent number
US09394455B2

Reaction notes

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