Acetone → Propylene glycol methyl ether acetate

HRID 2356182Notes

Reaction equation

HRID 2356182 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].C(N(CC)CC)C.[C:12](Cl)(=[O:19])[C:13]1C=CC=CC=1.C(O)(=O)[C:22](O)=[O:23]>C(OCC)(=O)C>[C:12]([O:3][CH:2]([CH3:4])[CH2:1][O:23][CH3:22])(=[O:19])[CH3:13]

Participants

6

Reactant 4

HCID 180AcetoneHCID 971Oxalic AcidHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 7946Propylene glycol methyl ether acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a four-necked flask equipped with a condenser, a stirrer and a thermometer, 174.5 parts of the resin obtained and 1,047 parts of acetone were charged to obtain a solution. To the solution, 19.7 parts of triethylamine was added and the resultant mixture was heated to 40° C. To the mixture, 18.3 parts of benzoyl chloride was added dropwise over 30 minutes and the resultant mixture was kept at 40° C. for 3 hours. The obtained mixture was mixed with 698 parts of ethyl acetate and 640 parts of 0.5% aqueous solution of oxalic acid. the resultant mixture was separate to obtain the organic layer and the aqueous layer. The organic later obtained washed with an aqueous solution of oxalic acid. The obtained organic layer was mixed with 698 parts of ethyl acetate, 698 parts of propylene glycol methyl ether acetate and 436 parts of water. The resultant mixture was stirred and separated to obtain the organic layer. The organic layer was washed four times with water and concentrated under reduced pressure. The residue was mixed with propylene glycol methyl ether acetate to concentrate under reduced pressure to obtain 543 parts of a propylene glycol methyl ether acetate solution containing the resin (the content of the solid: 33.7%). The resin obtained is called as A1.

Workup

  1. customInto a four-necked flask equipped with a condenser, a stirrer
  2. customa thermometer, 174.5 parts of the resin obtained
  3. customto obtain a solution
  4. customthe resultant mixture was separate
  5. customto obtain the organic layer
  6. customThe organic later obtained
  7. washwashed with an aqueous solution of oxalic acid
  8. additionThe obtained organic layer was mixed with 698 parts of ethyl acetate, 698 parts of propylene glycol methyl ether acetate and 436 parts of water
  9. customseparated
  10. customto obtain the organic layer
  11. washThe organic layer was washed four times with water
  12. concentrationconcentrated under reduced pressure
  13. additionThe residue was mixed with propylene glycol methyl ether acetate
  14. concentrationto concentrate under reduced pressure

Sources & evidence

ORD record
ord-7463fa34fa884064901b689c3386d4b1
Source dataset
uspto-grants-2010_07
Patent number
US07759045B2

Reaction notes

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