p-Toluenesulfonic acid → Propylene glycol methyl ether acetate

HRID 2191191Notes

Reaction equation

HRID 2191191 reaction equation
[CH:1]([O:3][CH2:4][CH3:5])=[CH2:2].[C:6]([O:9][CH2:10][CH3:11])(=[O:8])[CH3:7].[C:12]1([CH3:22])[CH:17]=[CH:16]C(S(O)(=O)=O)=[CH:14][CH:13]=1>C(N(CC)CC)C>[CH2:1]([O:3][CH2:4][CH2:5][O:9][C:10]1[CH:11]=[CH:22][C:12]([CH:17]=[CH2:16])=[CH:13][CH:14]=1)[CH3:2].[OH:3][C:4]1[CH:5]=[CH:22][C:12]([CH:17]=[CH2:16])=[CH:13][CH:14]=1.[C:6]([O:9][CH:10]([CH3:12])[CH2:11][O:3][CH3:1])(=[O:8])[CH3:7]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8023Ethyl vinyl etherHCID 8857Ethyl Acetate

Product 2

HCID 7946Propylene glycol methyl ether acetateHCID 131719558p-1-Ethoxyethoxystyrene p-hydroxystyrene

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into a 500 ml-volume three-neck flask, 72.1 g of poly-4-hydroxystyrene (VP-8000, produced by Nippon Soda Co., Ltd.), 16.4 g of ethyl vinyl ether and 300 ml of ethyl acetate were charged. A catalytic amount of para-toluenesulfonic acid was added, and reaction was allowed to proceed at room temperature for 3 hours in a nitrogen stream. After adding a small amount of triethylamine, the solution was washed with pure water. Propylene glycol monomethyl ether acetate was added to the ethyl acetate layer, and ethyl acetate was removed by distillation under reduced pressure to obtain Polymer A′-11 (p-1-ethoxyethoxystyrene/p-hydroxystyrene) as a propylene glycol monomethyl ether acetate solution.

Workup

  1. customreaction
  2. washthe solution was washed with pure water
  3. additionPropylene glycol monomethyl ether acetate was added to the ethyl acetate layer, and ethyl acetate
  4. customwas removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-0d36c7dc676e41d38313c4e4d1d77f4b
Source dataset
uspto-grants-2012_12
Patent number
US08329380B2

Reaction notes

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