2-Methylbenzenesulfonic acid → HCID 18326000, compound

HRID 2379378Notes

Reaction equation

HRID 2379378 reaction equation
C[Si](C)(C)O[C:4]1[CH:20]=[CH:19][C:7]([C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=1.OC1C=[CH:39][C:27]([C:28]([O:30]C2C=CC(CC)=CC=2)=[O:29])=[CH:26]C=1.C(OC(=O)C(C)=C)(=O)C(C)=C.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1.C(O)C>[C:28]([O:30][C:19]1[CH:20]=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=1)=[O:9])(=[O:29])[C:27]([CH3:39])=[CH2:26]

Participants

7

Reactant 4

HCID 69252-Methylbenzenesulfonic acidHCID 12974Methacrylic anhydrideHCID 137198734-Ethylphenyl 4-hydroxybenzoateHCID 539501834-Ethylphenyl 4-trimethylsilyloxybenzoate

Product 1

HCID 18326000HCID 18326000, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 16.9 g of 4-ethylphenyl 4-trimethylsilyloxybenzoate (prepared by the procedure in EP-A-358,208, page 9, sec. C) in 15 ml of toluene and 10 ml of ethanol was refluxed for 1 hour and then freed from volatile components by heating at 100° C. for 60 minutes. The remaining 13.3 g of 4-ethylphenyl 4-hydroxybenzoate were dissolved in 15 ml of toluene together with 30 g of methacrylic anhydride and 1.2 g of toluenesulfonic acid, and the mixture was heated at 100° C. for 1 hour. After cooling, the product was precipitated with hexane and recrystallized from ethanol.

Workup

  1. temperaturethe mixture was heated at 100° C. for 1 hour
  2. temperatureAfter cooling
  3. customthe product was precipitated with hexane
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-702f6a7665d840f99fd64dc626ae4b28
Source dataset
uspto-grants-1994_11
Patent number
US05362315

Reaction notes

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