Pyridine → 3-hydroxy-4-propoxybenzaldehyde O-methyloxime

HRID 2236438Notes

Reaction equation

HRID 2236438 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH3:13])[CH:5]=O.N1C=CC=CC=1.Cl.[O:21]([NH2:23])[CH3:22]>O>[CH3:22][O:21][N:23]=[CH:5][C:4]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][CH3:13])=[C:2]([OH:1])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 219461763-Hydroxy-4-propoxybenzaldehyde

Product 1

HCID 748285453-hydroxy-4-propoxybenzaldehyde O-methyloximeYield 120.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An amount of 3-hydroxy-4-propoxybenzaldehyde (150 mg, 0.83 mmol) is added pyridine (4.0 ml) at room temperature, followed by addition of methoxylamine hydrogen chloride (101.2 mg, 1.2 mmol). The mixture is stirred at ambient temperature for 24 h, and 4 mL of water is added. After the solvents were evaporated, the residue is dissolved 8 mL of anhydrous ether, washed successively with 2 mL of aqueous sodium bicarbonate, 2 mL of sodium bisulfite, and 2 mL of brine. Dried over magnesium sulfate, evaporated to give a yellow solid (210 mg). MS (ESI) m/z 210.5 (M+1)

Workup

  1. customAfter the solvents were evaporated
  2. dissolutionthe residue is dissolved 8 mL of anhydrous ether
  3. washwashed successively with 2 mL of aqueous sodium bicarbonate, 2 mL of sodium bisulfite, and 2 mL of brine
  4. dry with materialDried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-772923fef9d840c2934f5eb91cbe0138
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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