Ethylene Glycol → 5-[1,3]Dioxolan-2-yl-N-methyl-N-propyl-isophthalamic acid

HRID 732529Notes

Reaction equation

HRID 732529 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2].C(O)C[OH:23].B(F)(F)F.CCOCC.[OH-].[Na+]>C1COCC1.O>[O:3]1[CH2:1][CH2:2][O:20][CH:4]1[C:5]1[CH:6]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:15]=[C:16]([CH:17]=1)[C:18]([OH:23])=[O:19]

Participants

7

Reactant 4

HCID 174Ethylene Glycol2×HCID 8000Boron trifluoride etherateHCID 14798Sodium Hydroxide2×HCID 86615013HCID 86615013, compound

Product 1

HCID 688187915-[1,3]Dioxolan-2-yl-N-methyl-N-propyl-isophthalamic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Mix 5-formyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (580 mg, 2.1 mmol), ethane-1,2-diol (0.35 mL, 6.3 mmol), and boron trifluoride diethyl etherate (0.2 mL, 1.6 mmol) in THF (5 mL) and stir for 1.5 h. Add additional ethane-1,2-diol (0.35 mL, 6.3 mmol) and stir for 20 min. Add 1 N NaOH (10 mL) and stir for 1 h. Add additional 5 N NaOH (1 mL) and stir for 30 min. Dilute the reaction mixture with water (10 mL) and wash with diethyl ether (2×10 mL). Acidify the aqueous layer with 0.5 N HCl to about pH=5. Extract with dichloromethane (3×20 mL), dry (sodium sulfate) and concentrate to give the title compound as a crude residue that is used in the next step without further purification.

Workup

  1. stirringstir for 20 min
  2. stirringstir for 1 h
  3. stirringstir for 30 min
  4. washwash with diethyl ether (2×10 mL)
  5. extractionExtract with dichloromethane (3×20 mL)
  6. dry with materialdry (sodium sulfate)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-6918f645db69498591a61dfb9ec63d31
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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