2-Ethylhexanol → 391900-25-7

HRID 2294647Notes

Reaction equation

HRID 2294647 reaction equation
[C:1]([OH:14])(=[O:13])/[CH:2]=[CH:3]/[C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1.[CH2:15]([CH:17]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:18]O)[CH3:16]>C1(C)C=CC=CC=1>[C:1]([O:14][CH2:18][CH:17]([CH2:15][CH3:16])[CH2:20][CH2:21][CH2:22][CH3:23])(=[O:13])/[CH:2]=[CH:3]/[C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1

Participants

4

Reactant 2

HCID 77202-EthylhexanolHCID 445858Ferulic Acid

Product 1

HCID 11961066391900-25-7Yield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In a three-necked flask, 19.5 g (0.1 mole) of ferulic acid, 13.0 g (0.1 mole) of 2-ethylhexanol, and 200 ml of toluene as a solvent were placed, and 1.0 g of paratoluenesulfonic acid as an acid catalyst was added. This reaction mixture was stirred at 80° C. for 13 hours. After cooled, the mixture was washed with saturated aqueous solution of sodium hydrogen carbonate. The organic layer was dried over anhydrous magnesium sulfate, and decolored by activated carbon. The solvent toluene was fully evaporated off from the organic layer under reduced pressure to obtain 25.5 g (yield: 85%) of 2-ethylhexyl ferulate.

Workup

  1. temperatureAfter cooled
  2. washthe mixture was washed with saturated aqueous solution of sodium hydrogen carbonate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent toluene was fully evaporated off from the organic layer under reduced pressure

Sources & evidence

ORD record
ord-ab20957f09a94e60bd406dba8f08a388
Source dataset
uspto-grants-1997_11
Patent number
US05688991

Reaction notes

Loading…