Benzyl Alcohol → Benzyl acrylate

HRID 2226590Notes

Reaction equation

HRID 2226590 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].COC1C=CC(O)=CC=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18](S(O)(=O)=O)=[CH:17][CH:16]=1.C(O)C1C=CC=CC=1>O>[C:1]([O:5][CH2:25][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 6101p-Toluenesulfonic acidHCID 6581Acrylic AcidHCID 90154-Methoxyphenol

Product 1

HCID 75617Benzyl acrylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

144 g (2 mols) of acrylic acid, which have been inhibited with 1.4 g of hydroquinone monomethyl ether, are dissolved in 139 g of a high-boiling aromatics mixture in a 1 l four-necked flask with stirrer, contact thermometer, water separator and gas inlet tube. 3.2 g of p-toluenesulfonic acid are added thereto, the mixture is heated to 70° C. and, at this temperature, 216 g (2 mols) of benzyl alcohol are allowed to run in over a period of 10 minutes. After the end of the addition, the mixture is heated to reflux. To accelerate the removal of water, air is passed through the solution. The reaction is complete after about 5 hours. The progress of the reaction is monitored via the acid number. After 5 hours, the latter gives a conversion of about 97%.

Workup

  1. customto run in over a period of 10 minutes
  2. additionAfter the end of the addition
  3. temperaturethe mixture is heated to reflux
  4. customthe removal of water, air
  5. waitAfter 5 hours
  6. customthe latter gives a conversion of about 97%

Sources & evidence

ORD record
ord-44b5f6f38f3242059f62eafb0caaf50f
Source dataset
uspto-grants-1994_09
Patent number
US05349019

Reaction notes

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