2-Methoxyethanol → HCID 86755721, compound

HRID 1952697Notes

Reaction equation

HRID 1952697 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[CH2:2].[Cl-:12].[CH:13]([CH2:15][N+:16]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:18])[CH3:17])=[CH2:14].COCCO>C(OCC)(=O)C>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[CH2:2].[Cl-:12].[CH:13]([CH2:15][N+:16]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([CH3:18])[CH3:17])=[CH2:14]

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 140984-Vinylbenzoic acidHCID 11287299Benzenemethanaminium, N,N-dimethyl-N-2-propenyl-, chloride

Product 1

HCID 86755721HCID 86755721, compoundYield 250.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 1 liter three-necked flask were put 146.9 g (0.99 mol) of p-vinylbenzoic acid (available from Hokko Chemical Industry Co., Ltd.), 44.2 g (0.21 mol) of vinylbenzyltrimethylammonium chloride, and 446 g of 2-methoxyethanol, and the resulting mixture was heated to 75° C. while stirring in a nitrogen stream. Then, 2.76 g (12 mmol) of dimethyl 2,2-azobis(isobutyrate) was added to the mixture kept at 75° C., and the stirring was continued. After stirring for 2 hours, 2.76 g (12 mmol) of dimethyl 2,2-azobis(isobutyrate) was added, and the stirring was continued. After 2 hours, 2.76 g (12 mmol) of dimethyl 2,2-azobis(isobutyrate) was added thereto, and the stirring was further continued for an additional 2 hour period. After allowing to cool to room temperature, the reaction mixture was poured into 12 liters of ethyl acetate while stirring. The precipitated solid was collected by filtration and dried to obtain 189.5 g of a solid product. The product was found to have a weight average molecular weight (Mw) of 32,000 as measured by a light scattering method.

Workup

  1. customIn a 1 liter three-necked flask were put
  2. customkept at 75° C.
  3. stirringAfter stirring for 2 hours
  4. waitthe stirring was further continued for an additional 2 hour period
  5. stirringwhile stirring
  6. filtrationThe precipitated solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-16fd5e6e8dcb4e9696b0d724b90ef01f
Source dataset
uspto-grants-2000_09
Patent number
US06114089

Reaction notes

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