Dichloromethane → HCID 19777598, compound

HRID 1613016Notes

Reaction equation

HRID 1613016 reaction equation
Cl[CH:2]([O:10][CH2:11][CH3:12])[CH:3]([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].[C:13]([O-:21])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na+].C(Cl)Cl>CN(C)C=O.CCOCC>[C:13]([O:21][CH:2]([O:10][CH2:11][CH3:12])[CH:3]([O:4][CH2:5][CH3:6])[O:7][CH2:8][CH3:9])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 517055Sodium BenzoateHCID 19777600HCID 19777600, compound

Product 1

HCID 19777598HCID 19777598, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 178 mg (0.905 mmole) of 1-chloro-1,2,2-triethoxyethane (produced in accordance with Example IV) and 206 mg (1.43 mmoles) of sodium benzoate in 3.00 mL of N,N-dimethylformamide, spectrophotometric-grade, commercially available from Aldrich Chemical Co., Milwaukee, Wis., was stirred, while being protected from exposure to atmospheric moisture, at room temperature for 21 hours. The mixture was diluted with 20 mL of 3:1 (volume/volume) ether:methylene chloride; and the organic layer was washed five times with 25 mL portions of I0% aqueous sodium chloride to ensure removal of dimethylformamide. The washed organic layer was subsequently dried over anhydrous sodium sulfate and filtered. Removal of the volatile organic material under reduced pressure afforded 212 mg (83% yield) of the title compound, the identity and purity of which were ascertained by proton NMR analysis [two doublets (J=5.5 Hz), one at δ4.63 (CH3CH2OCHOCH2CH3), the other at δ6.07 (CHOC(=O)C6H5)]. The title compound was subsequently saponified by use of potassium carbonate (2 equivalents) in 4:1 (volume/volume) methanol:water at 0° C. for 5 hours to afford glyoxal mono(diethyl acetal) and the corresponding hydrate (CH3CH2O)2CHCH(OH)2 and hemiacetal ##STR10## in high yield. Heating the latter mixture in toluene as described in Example XVIII affords glyoxal mono(diethyl acetal) as methanol and water are distilled out of the mixture.

Workup

  1. washand the organic layer was washed five times with 25 mL portions of I0% aqueous sodium chloride
  2. customremoval of dimethylformamide
  3. dry with materialThe washed organic layer was subsequently dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customRemoval of the volatile organic material under reduced pressure

Sources & evidence

ORD record
ord-114e720d4ea94ac097d3ee8d55d2601f
Source dataset
uspto-grants-1993_03
Patent number
US05191127

Reaction notes

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