Hydrochloric Acid → HCID 19261375, compound

HRID 1951977Notes

Reaction equation

HRID 1951977 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].Cl>[Cu]Cl.C(O)CCC>[CH2:5]([O:6][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6])[CH2:4][CH2:3][CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 763083-Bromo-4-hydroxybenzaldehyde

Product 1

HCID 19261375HCID 19261375, compoundYield 161.1%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

4.3 g (188 mmol) of sodium is put at the bottom of a flask under nitrogen and 40 ml of 1-butanol is poured on top. The reaction mixture is stirred and heated progressively up to 120° C.; as the butanolate formed is sparingly soluble, 20 ml of 1-butanol is added. When all the sodium has been consumed, the reaction mixture is brought back to room temperature and 40 ml of dimethylformamide is added. Under nitrogen, 6.8 g (68.2 mmol) of copper(I) chloride is added and then 12.4 g (62 mmol) of 3-bromo-4-hydroxy-benzaldehyde. The reaction mixture is heated progressively to 120° C. and stirred for 2 hours. After cooling to room temperature and then acidifying to pH5 with aqueous hydrochloric acid of concentration 2M, the reaction mixture is extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated. After trituration and then recrystallization of the residue from pentane, 9.7 g (81%) of 3-butoxy-4-hydroxy-benzaldehyde is obtained.

Workup

  1. customWhen all the sodium has been consumed
  2. customis brought back to room temperature
  3. addition40 ml of dimethylformamide is added
  4. temperatureAfter cooling to room temperature
  5. extractionthe reaction mixture is extracted with ethyl acetate
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customAfter trituration and then recrystallization of the residue from pentane

Sources & evidence

ORD record
ord-fb424e7dc84544c98e088d47ee6fc794
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

Loading…