Toluene → HCID 21997113, compound

HRID 1977000Notes

Reaction equation

HRID 1977000 reaction equation
C1(C)C=CC=CC=1.[CH2:8]([O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][OH:17])=[CH:14][CH:13]=1)[CH:9]=[CH2:10].[C:20](O)(=[O:24])[C:21]([CH3:23])=[CH2:22]>COC1C=CC(O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:20]([O:17][CH2:16][C:15]1[CH:18]=[CH:19][C:12]([O:11][CH2:8][CH:9]=[CH2:10])=[CH:13][CH:14]=1)(=[O:24])[C:21]([CH3:23])=[CH2:22]

Participants

7

Reactant 3

HCID 1140TolueneHCID 4093Methacrylic AcidHCID 11744970(4-(Prop-2-en-1-yloxy)phenyl)methanol

Product 1

HCID 21997113HCID 21997113, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 90154-MethoxyphenolCatalystHCID 962WaterSolvent2×

Procedure

To a 250 ml reaction flask fitted with a Dean-Stark water trap, condenser and magnetic stirrer was added toluene (100 ml), 4allyloxybenzyl alcohol (30.0 g; 0.18 moles), methacrylic acid (15.7 g; 0.18 moles), 4-methoxyphenol (0.6 g) and p-toluene sulfonic acid (0.23 g). The stirred solution was heated under reflux until all of the water was removed (2 hours). The solution was cooled and washed with an equal volume of sodium bicarbonate solution and then with sodium chloride solution. The organic layer was dried over magnesium sulfate and the solvent removed by distillation under reduced pressure to yield 4-allyloxybenzyl methacrylate (33.6 g; 81% yield) as an orange colored viscous liquid.

Workup

  1. customTo a 250 ml reaction flask
  2. temperatureThe stirred solution was heated
  3. customwas removed (2 hours)
  4. temperatureThe solution was cooled
  5. washwashed with an equal volume of sodium bicarbonate solution
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customthe solvent removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-755ad47be2b541b28d06f19bf81a75b8
Source dataset
uspto-grants-2001_05
Patent number
US06231714B1

Reaction notes

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