2-Methylbenzenesulfonic acid → HCID 18326000, compound

HRID 399884

Reaction equation

HRID 399884 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 13719873HCID 13719873, compoundHCID 53950183HCID 53950183, compound

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 according to the instructions in EP-A-0 358 205, page 9, section C) in 15 ml of toluene and 10 ml of ethanol was boiled under reflux for one hour and then freed from volatile constituents by heating at 100° C. for 60 minutes. The 13.3 g of 4-ethylphenyl 4-hydroxybenzoate which remained were dissolved, together with 30 g of methacrylic anhydride and 1.2 g of toluenesulfonic acid, in 15 ml of toluene and the solution was heated at 100° C. for 1 hour. After cooling, the product was precipitated with hexane and recrystallized from ethanol.

Workup

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

Sources & evidence

ORD record
ord-6b267d8fecba4701972798274e4568d9
Source dataset
uspto-grants-1998_10
Patent number
US05824733

Linked notes

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