Methyl Isobutyl Ketone → p-1-Ethoxyethoxystyrene p-hydroxystyrene

HRID 2120030Notes

Reaction equation

HRID 2120030 reaction equation
[CH:1]#[C:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(C(C)=O)C(C)C.[CH:29]([O:31][CH2:32][CH3:33])=[CH2:30]>O>[CH2:29]([O:31][CH2:32][CH2:33][O:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[CH2:1])=[CH:4][CH:5]=1)[CH3:30].[OH:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[CH2:1])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl Ketone2×HCID 8023Ethyl vinyl etherHCID 327584-Ethynylphenol2×HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 131719558p-1-Ethoxyethoxystyrene p-hydroxystyrene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Into a flask were charged 108.3 g of a solution of poly(p-hydroxystyrene)(weight-average molecular weight: about 15200, degree of dispersion: 1.20 (GPC method: reduced by polystyrene), 30.0 g as the weight of poly(p-hydroxystyrene)), 0.005 g of p-toluenesulfonic acid monohydrate and 102 g of methyl isobutyl ketone, and the mixture was stirred. Into this resin solution was dropped 8.7 g of ethyl vinyl ether (0.12 mol, 0.48 equivalent based on hydroxyl groups in poly(p-hydroxystyrene)) using a dropping funnel. The mixture was stirred at 25° C. for 3 hours, then, to this was added 15 g of methyl isobutylketone and 57 g of ion exchanged water, and the solution was separated. Further, the resulted organic layer was washed with 57 g of ion exchanged water and separated, four times.

Workup

  1. customthe solution was separated
  2. washFurther, the resulted organic layer was washed with 57 g of ion
  3. customseparated

Sources & evidence

ORD record
ord-95972876bd2d4b5392884bee5e15eb8a
Source dataset
uspto-grants-2004_02
Patent number
US06689531B2

Reaction notes

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