Water → HCID 53967443, compound

HRID 649487Notes

Reaction equation

HRID 649487 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1C(=C)C(O)=O.[CH2:11]([CH:13]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:14]O)[CH3:12].[OH2:20]>>[C:2]([O:1][C:2]1[O:1][CH:5]=[CH:4][C:3]=1[CH2:14][CH:13]([CH2:11][CH3:12])[CH2:16][CH2:17][CH2:18][CH3:19])(=[O:20])[CH:3]=[CH2:4]

Participants

4

Reactant 3

HCID 962WaterHCID 77202-EthylhexanolHCID 3162592-(Furan-2-yl)prop-2-enoic acid

Product 1

HCID 53967443HCID 53967443, compoundYield 92.6%

Conditions

Temperature
190 °C

Procedure

Furylacrylic acid (23 g, 0.135 mol), 2-ethylhexanol (87.5 g, 0.67 mol) and 0.5 ml Tyzor® (DuPont tetraisopropyltitanate) were mixed in a 3-neck round bottom flask equipped with a thermometer, condenser and high speed stirrer. The mixture was heated to 190° C. and held there with stirring until the theoretical 2.4 ml of water was distilled off at atmospheric pressure. The residual product was distilled at 134° C./0.5 torr yielding 33.0 g (92.6%) of 2-ethylhexylfuryl acrylate. A gas chromatagraphic analysis indicated the product was 97.1% pure. The material has peak absorption at 300.1 nm and a K of 98.3.

Workup

  1. customequipped with a thermometer, condenser and high speed stirrer
  2. distillationwas distilled off at atmospheric pressure
  3. distillationThe residual product was distilled at 134° C./0.5 torr

Sources & evidence

ORD record
ord-7dbcca374080466fae41ba2191c39e88
Source dataset
uspto-grants-1988_04
Patent number
US04740369

Reaction notes

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