2-Ethylhexanol → 391900-25-7

HRID 1415659Notes

Reaction equation

HRID 1415659 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-c946be7bd0ba40bdb010f85aaa4d926d
Source dataset
uspto-grants-1999_06
Patent number
US05908615

Reaction notes

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