4-Hydroxybenzaldehyde → HCID 66671630, compound

HRID 446560Notes

Reaction equation

HRID 446560 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.[BH4-].[Na+].C(=O)([O-])O.[Na+]>C(O)C>[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][CH:12]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 516892Sodium BicarbonateHCID 571728Methyl 4-(aminomethyl)benzoateHCID 4311764Sodium borohydride

Product 1

HCID 66671630HCID 66671630, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 4-(Aminomethyl)benzoate (6.88 g, 34.2 mmol) and 4-hydroxybenzaldehyde (4.60 g, 37.7 mmol) were dissolved in ethanol (300 mL), the mixture was heated to reflux for 6 hours, sodium borohydride (2.07 g, 54.7 mmol) was added at room temperature, and the mixture was stirred at room temperature for 1 hour. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with dichloromethane. The resulting organic layer was washed with saturated sodium chloride solution and dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was reprecipitated with dichloromethane-hexane to give the title compound (4.90 g; yield, 52%) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 6 hours
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe resulting organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was reprecipitated with dichloromethane-hexane

Sources & evidence

ORD record
ord-8ac04ea1793e4aa98a4165c97383e785
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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