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Oxalic Acid → Propylene glycol methyl ether acetate

HRID 252879
Notes
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Reaction equation

HRID 252879 reaction equation
[O:1]1[CH:7]2[CH:2]1CC(CC[Si](OC)(OC)OC)[CH2:5][CH2:6]2.COC([SiH3])(OC)OC.C1([Si](OC)(OC)OC)C=CC=CC=1.[C:38](O)(=O)[C:39]([OH:41])=[O:40]>CO.O>[C:39]([O:41][CH:6]([CH3:5])[CH2:7][O:1][CH3:2])(=[O:40])[CH3:38]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 18137TrimethoxyphenylsilaneHCID 18819EpoxycyclohexylethyltrimethoxysilaneHCID 101924291Trimethoxymethyl silane

Product 1

HCID 7946Propylene glycol methyl ether acetateYield 100%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
2×
HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

In a 1000 ml glass flask, to a mixture of 150 g of methanol, 22 g of 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane, 77 g of trimethoxymethyl silane, 14 g of phenyl trimethoxy silane, and 1.5 g of oxalic acid was added dropwise a mixed solution of 40 g of deionized water and 20 g of methanol at a liquid temperature of 40 degrees C. After that, this solution was stirred for 12 hours at 40 degrees C. After the reaction finished, the solvent was removed under a reduced pressure. Thus-obtained residue was dissolved in 1000 ml of ethyl acetate, and washed with deionized water for washing. After the water layer was separated, the organic layer was washed twice with deionized water. To this organic layer was added 600 g of propylene glycol monomethyl ether acetate (PGMEA), and the contents were heated up to a liquid temperature of 40 degrees C. under a reduced pressure to remove ethyl acetate and to give a PGMEA solution of a polymer.

Workup

  1. customthe solvent was removed under a reduced pressure
  2. dissolutionThus-obtained residue was dissolved in 1000 ml of ethyl acetate
  3. washwashed with deionized water
  4. washfor washing
  5. customAfter the water layer was separated
  6. washthe organic layer was washed twice with deionized water
  7. additionTo this organic layer was added 600 g of propylene glycol monomethyl ether acetate (PGMEA)
  8. temperaturethe contents were heated up to a liquid temperature of 40 degrees C
  9. customunder a reduced pressure to remove ethyl acetate

Sources & evidence

ORD record
ord-edda5971751b461a9969fe51bbc46dfe
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07868407B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes