Acetone → 3,4-Bis(2-methoxyethoxy)benzaldehyde

HRID 1801689Notes

Reaction equation

HRID 1801689 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].I[CH2:12][CH2:13][O:14][CH3:15].[C:16](=[O:19])([O-])[O-].[K+].[K+].[CH3:22][C:23](C)=O>>[CH3:15][O:14][CH2:13][CH2:12][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:22][CH2:23][O:19][CH3:16])[CH:5]=[O:6]

Participants

5

Reactant 4

HCID 180AcetoneHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 791361-Iodo-2-methoxyethane

Product 1

HCID 160633913,4-Bis(2-methoxyethoxy)benzaldehydeYield 47%

Conditions

Temperature
27.5 °C

Procedure

80.0 g (0.57 mol) of 3,4-dihydroxy benzaldehyde and 800.0 ml of acetone were charged into 2.0 L4 necked round bottom flask, connect to a mechanical stirrer, thermo meter socket and condenser at 25-30° C. Reaction mass was stirred for 20 min. 324.0 g (1.74 mol) of 1-iodo-2-methoxy-ethane and 240.0 g (1.70 mol) of potassium carbonate were charged. Reaction mass was heated to reflux. Reaction mass temperature was maintained at reflux for 6 hours. Reaction mass temperature was cooled to 25-30° C. and inorganic solid was filtered. Acetone was completely distilled under vacuum at below 60° C. Remaining mass was diluted with 400.0 ml of DM water. Compound was extracted with 400.0 ml of ethyl acetate and organic layer was dried with sodiumsulphate. Ethyl acetate was completely distilled under vacuum and finally applied high vacuum at below 60° C. 69.20 g of crude product (Oil) was obtained (yield: 47.0% by theory).

Workup

  1. customconnect to a mechanical stirrer
  2. customat 25-30° C
  3. customReaction mass
  4. customReaction mass
  5. temperaturewas heated to reflux
  6. customReaction mass temperature
  7. temperaturewas maintained
  8. temperatureat reflux for 6 hours
  9. customReaction mass temperature
  10. filtrationinorganic solid was filtered
  11. distillationAcetone was completely distilled under vacuum at below 60° C
  12. additionRemaining mass was diluted with 400.0 ml of DM water
  13. extractionCompound was extracted with 400.0 ml of ethyl acetate and organic layer
  14. dry with materialwas dried with sodiumsulphate
  15. distillationEthyl acetate was completely distilled under vacuum and finally applied high vacuum at below 60° C

Sources & evidence

ORD record
ord-334c7801aba444abb202fde45e495260
Source dataset
uspto-grants-2013_01
Patent number
US08349847B2

Reaction notes

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