Ethanol → Methacrolein diethylacetal

HRID 1769063Notes

Reaction equation

HRID 1769063 reaction equation
O=[CH:2][C:3](=C)[CH3:4].C(O)C.C(O[CH:12]([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])C>C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>[CH2:17]([O:16][CH:12]([O:13][CH2:14][CH3:15])[C:3](=[CH2:2])[CH3:4])[CH3:18]

Participants

7

Reactant 3

HCID 702EthanolHCID 6562MethacroleinHCID 31214Ethyl orthoformate

Product 1

HCID 11194409Methacrolein diethylacetalYield 404.5%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 11430Potassium CarbonateCatalystHCID 6344DichloromethaneSolvent

Procedure

p-Toluenesulfonic acid (1.14 g, 0.006 mol) was added to a mixture of methacrolein (42.35 g, 0.06 mol), ethanol (141.9 mL), CH2Cl2 (120 mL) and triethylorthoformate (130.6 mL, 0.785 mol). The mixture was stirred at room temperature for 3 days and then K2CO3 (2 g) was added. The mixture was stirred for 10 minutes, filtered, and then the filtrate was concentrated in vacuo. The residue was purified by distillation through a Vigreaux column at 130° C. to afford 35 g of methacrolein diethylacetal.

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. distillationThe residue was purified by distillation through a Vigreaux column at 130° C.

Sources & evidence

ORD record
ord-c242999875e24297bc3dcc641e9fa88f
Source dataset
uspto-grants-1995_01
Patent number
US05380729

Reaction notes

Loading…