Ethyl Acetate → Propylene glycol methyl ether acetate

HRID 1027340Notes

Reaction equation

HRID 1027340 reaction equation
C#CC1[CH:8]=[CH:7][C:6]([OH:9])=CC=1.[C:10](=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+].[C:18]([O:21]CC)(=[O:20])[CH3:19]>CS(C)=O.ClCC1C=CC(C2C=CC=CC=2)=CC=1.[I-].[Na+].COC(Cl)C1C=CC=CC=1.O>[CH3:8][CH:7]([O:21][C:18]([CH3:19])=[O:20])[CH2:6][O:9][CH3:10]

Participants

10

Reactant 4

HCID 8857Ethyl Acetate2×HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 327584-Ethynylphenol

Product 1

HCID 7946Propylene glycol methyl ether acetate

Reagents, catalysts & solvents 5

HCID 5238Sodium IodideCatalystHCID 154634-Phenylbenzyl chlorideCatalystHCID 11062637Methoxybenzyl chlorideCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

30 g of poly(p-hydroxystyrene) (VP8000) produced by Nippon Soda Co., Ltd. was dissolved in 120 mL of dimethylsulfoxide (DMSO), and 3.04 g of 4-chloromethylbiphenyl, 34.51 g of potassium carbonate and 0.56 g of sodium iodide were added thereto. The mixture was stirred at 70° C. for 4 hours, and the reaction solution was returned to room temperature. Subsequently, 8.21 g of α-chlorobenzyl methyl ether was added dropwise thereto and after stirring at room temperature for 4 hours, 100 mL of ethyl acetate and 100 mL of distilled water were added thereto. Thereafter, 130 g of an aqueous 21 mass % ammonium chloride solution was little by little added to the reaction solution while stirring the reaction solution in ice water. The reaction solution was transferred to a separating funnel, and 100 mL of ethyl acetate and 100 mL of distilled water were further added. After stirring, the aqueous layer was removed, and the organic layer was washed with 200 mL of distilled water five times. The organic layer was then concentrated to about 150 mL and added dropwise in 2 L of hexane. A part of the obtained precipitate was sampled for NMR measurement, and the remaining was dissolved in 70 g of PGMEA. From the obtained solution, the low boiling point solvent was removed by an evaporator to obtain 100.1 g of a PGMEA solution (33.8 mass %) of Resin (P-4).

Workup

  1. customwas returned to room temperature
  2. stirringafter stirring at room temperature for 4 hours
  3. additionby little added to the reaction solution
  4. customThe reaction solution was transferred to a separating funnel
  5. stirringAfter stirring
  6. customthe aqueous layer was removed
  7. washthe organic layer was washed with 200 mL of distilled water five times
  8. concentrationThe organic layer was then concentrated to about 150 mL
  9. additionadded dropwise in 2 L of hexane
  10. aliquotA part of the obtained precipitate was sampled for NMR measurement
  11. dissolutionthe remaining was dissolved in 70 g of PGMEA
  12. customFrom the obtained solution, the low boiling point solvent was removed by an evaporator

Sources & evidence

ORD record
ord-5206535831174a4296f3df3f57e13225
Source dataset
uspto-grants-2014_05
Patent number
US08735048B2

Reaction notes

Loading…