Toluene → HCID 58527985, compound

HRID 1473741Notes

Reaction equation

HRID 1473741 reaction equation
[CH2:1]=[C:2]([CH3:4])[CH3:3].[C:5]([O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)(=[O:9])[C:6]([CH3:8])=[CH2:7].C1(C)C=CC=CC=1>CS(O)(=O)=O.O>[C:5]([O:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:2]([CH3:4])([CH3:3])[CH3:1])=[CH:15][CH:16]=1)(=[O:9])[C:6]([CH3:8])=[CH2:7]

Participants

6

Reactant 3

HCID 1140TolueneHCID 8255IsobutyleneHCID 931522-Propenoic acid, 2-methyl-, 4-hydroxyphenyl ester

Product 1

HCID 58527985HCID 58527985, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 962WaterSolvent

Procedure

Under ice cooling, isobutene was introduced into a mixture of 17.8 g of 4-hydroxyphenyl methacrylate, 0.3 g of methanesulfonic acid, and 100 g of toluene over 4 hours. To the reaction solution, 50 g of water was added to quench the reaction, from which the organic layer was recovered. The organic layer was washed with water, sodium bicarbonate water, and saturated saline solution in sequence and concentrated. The concentrate was purified by distillation, obtaining 152 g (yield 65%) of 4-tert-butoxyphenyl methacrylate, designated Monomer 1.

Workup

  1. customto quench
  2. customthe reaction
  3. customfrom which the organic layer was recovered
  4. washThe organic layer was washed with water, sodium bicarbonate water, and saturated saline solution in sequence
  5. concentrationconcentrated
  6. distillationThe concentrate was purified by distillation

Sources & evidence

ORD record
ord-102099f2ef274e0ba22c242166d8e7ef
Source dataset
uspto-grants-2015_04
Patent number
US09017918B2

Reaction notes

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