Methanol → SBB056554

HRID 974739Notes

Reaction equation

HRID 974739 reaction equation
[C:1]([OH:12])(=[O:11])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][C:8]([OH:10])=O.[C:13](=O)(O)[O-].[Na+].[CH3:18][OH:19]>>[CH3:18][O:19][C:8](=[O:10])[CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][C:1]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 900393,6-Dioxaoctandioic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 4534693SBB056554

Procedure

Esterification of the crude 3,6-dioxaoctanedioic acid was accomplished as follows: To the reaction flask containing 36 g of the crude diacid, was added 110 ml of methanol. This was stirred for 3 days at room temperature after which 15 g of sodium bicarbonate was added and stirred overnight. The mixture was filtered to remove solids. To the liquor was added an additional 10 g of sodium bicarbonate; this mixture was stirred overnight. The mixture was again filtered; the liquor was fractionally distilled. NMR analysis of the esterified product showed a mixture of dimethyl triglycolate (78.4 mole %) and monomethyltriglycolate (21.6 mole %). No significant condensation of diacid was observed.

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. customto remove solids
  4. additionTo the liquor was added an additional 10 g of sodium bicarbonate
  5. stirringthis mixture was stirred overnight
  6. filtrationThe mixture was again filtered
  7. distillationthe liquor was fractionally distilled
  8. additiona mixture of dimethyl triglycolate (78.4 mole %) and monomethyltriglycolate (21.6 mole %)
  9. customNo significant condensation of diacid

Sources & evidence

ORD record
ord-e398193f2ccc4622b235568a94a677bc
Source dataset
uspto-grants-1997_03
Patent number
US05607687

Reaction notes

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