Methanol → 2,2-diethoxyethyl Benzoate

HRID 31710

Reaction equation

HRID 31710 reaction equation
N1C=CC=CC=1.[CH2:7]([O:9][CH:10]([O:13][CH2:14][CH3:15])[CH2:11][OH:12])[CH3:8].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CO>C(OCC)(=O)C.O>[C:16]([O:12][CH2:11][CH:10]([O:13][CH2:14][CH3:15])[O:9][CH2:7][CH3:8])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 121292,2-Diethoxyethanol

Product 1

HCID 118172582,2-diethoxyethyl BenzoateYield 96.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a pyridine (30 ml) solution of glycol aldehyde diethylacetal (19.8 g, 148 mmol), benzoyl chloride (51.7 ml, 444 mmol) was added dropwise at −20 to 30° C. The mixture was stirred at room temperature for 167 hours and 50 minutes. After methanol and water were added to the mixture, extraction with ethyl acetate was performed. The obtained organic layer was washed with a saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogencarbonate solution, and a saturated saline solution. After dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and purified by silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/9). Thereafter, purification by silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/100, 1/30, 1/10) was performed again to obtain the title compound (34 g, yield: 96.4%) as a light green oil.

Workup

  1. washThe obtained organic layer was washed with a saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialAfter dried over anhydrous magnesium sulfate
  3. concentrationthe mixture was concentrated under reduced pressure
  4. custompurified by silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/9)
  5. customThereafter, purification
  6. washby silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/100, 1/30, 1/10)

Sources & evidence

ORD record
ord-b344b96185124106ab3614c124b56f56
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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