Hydroquinone → 2-Propenoic acid, (9Z)-9-octadecen-1-yl ester

HRID 2165807Notes

Reaction equation

HRID 2165807 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20](O)(=[O:23])[CH:21]=[CH2:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C=CC(O)=CC=1)O>O.C1(C)C(C)=CC=CC=1>[C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:23])[CH:21]=[CH2:22]

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 6581Acrylic AcidHCID 521998p-Toluenesulfonic acid monohydrateHCID 5284499Oleyl Alcohol

Product 1

HCID 64363912-Propenoic acid, (9Z)-9-octadecen-1-yl esterYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

To a 500 ml round bottom flask equipped with a stirrer, condenser, water trap and thermometer, was added oleyl alcohol (100 g, 0.373 moles), acrylic acid (27 g, 0.373) moles), p-toluenesulfonic acid monohydrate (1g, 1 wt%, hydroquinone (0.2 g, 0.2 wt%) and xylene (I00 ml). The reaction mixture was heated to reflux and maintained until no more water was collected (~4 hrs). The xylene solution was then concentrated to about half of its original volume. The crude product was then washed successively with water, saturated sodium bicarbonate solution, and then again with water. The organic solution was dried over sodium sulfate, filtered and the solvent evaporated under reduced pressure. The product was stabilized by 0.01 wt% of MEHQ. The yield was 80%.

Workup

  1. customTo a 500 ml round bottom flask equipped with a stirrer, condenser, water trap
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. customwas collected (~4 hrs)
  5. concentrationThe xylene solution was then concentrated to about half of its original volume
  6. washThe crude product was then washed successively with water, saturated sodium bicarbonate solution
  7. dry with materialThe organic solution was dried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-a744377fa36c4d2cbefc2a4e52b7981f
Source dataset
uspto-grants-1990_07
Patent number
US04941985

Reaction notes

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