Water → p-(1-(Cyclohexylethoxy)ethoxy)styrene p-Hydroxystyrene

HRID 2086527Notes

Reaction equation

HRID 2086527 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.C(N([CH2:15][CH3:16])CC)C.[C:17]([O:20][CH2:21][CH3:22])(=O)[CH3:18].O>C(OC(C)COC)(=O)C.CC(C)=O>[CH:16]1([CH2:18][CH2:17][O:20][CH:21]([O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=2)[CH3:22])[CH2:15][CH2:4][CH2:3][CH2:2][CH2:9]1.[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 624534-Vinylphenol

Product 1

HCID 86598586p-(1-(Cyclohexylethoxy)ethoxy)styrene p-Hydroxystyrene

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 7946Propylene glycol methyl ether acetateSolvent

Conditions

Temperature
20 °C

Procedure

In 320 g of propylene glycol monomethyl ether acetate (PGMEA) was dissolved by heating 70 g of p-hydroxystyrene (VP-8000, manufactured by Nippon Soda Co., Ltd.), and after dehydrating by vacuum distillation the solution was cooled to 20° C. To the solution were added 0.35 g of pyridinium-p-toluenesulfonate and 22.4 g of cyclohexane ethanol. Then, after slowly adding 17.5 g of tert-butyl vinyl ether to the solution, the reaction was carried out at 20° C. for 5 hours. To the reaction liquid were added 0.28 g of triethylamine and 320 ml of ethyl acetate and the mixture was washed three times with 150 ml of distilled water. The solvent was distilled off and the residue was concentrated. The oil obtained was dissolved in 100 ml of acetone and 2 liters of distilled water was slowly added to the solution. A powder deposited was collected by filtration and dried to obtained 54 g of the desired product.

Workup

  1. distillationafter dehydrating by vacuum distillation the solution
  2. additionTo the solution were added 0.35 g of pyridinium-p-toluenesulfonate and 22.4 g of cyclohexane ethanol
  3. additionThen, after slowly adding 17.5 g of tert-butyl vinyl ether to the solution
  4. customTo the reaction liquid
  5. washthe mixture was washed three times with 150 ml of distilled water
  6. distillationThe solvent was distilled off
  7. concentrationthe residue was concentrated
  8. customThe oil obtained
  9. filtrationA powder deposited was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-c45b98d8010941b095e1747446bafa3b
Source dataset
uspto-grants-2004_04
Patent number
US06727036B2

Reaction notes

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