1-(4-(Diethoxymethyl)phenyl)-n,n,-dimethylmethanamine → 4-Dimethylaminomethylbenzaldehyde

HRID 1467720Notes

Reaction equation

HRID 1467720 reaction equation
C([O:3][CH:4](OCC)[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]([CH3:14])[CH3:13])=[CH:7][CH:6]=1)C>Cl>[CH3:14][N:12]([CH2:11][C:8]1[CH:7]=[CH:6][C:5]([CH:4]=[O:3])=[CH:10][CH:9]=1)[CH3:13]

Participants

3

Reactant 1

HCID 230003481-(4-(Diethoxymethyl)phenyl)-n,n,-dimethylmethanamine

Product 1

HCID 1932514-DimethylaminomethylbenzaldehydeYield 82%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To the mixture of 1-(4-(diethoxymethyl)phenyl)-N,N-dimethylmethanamine (7.0 g, 29.5 mmol) in hydrogen chloride (3M in water 30 mL) was stirred at room temperature for 5 hr. Then the mixture was extracted with ethyl acetate (50 ml×3). The aqueous layer was basified with sodium carbonate to pH=10, extracted with ethyl acetate (50 ml×3), dried with anhydrous sodium sulfate, and concentrated to give crude product (3.95 g, yield 82%). LC-MS (ESI) m/z: 164 (M+1)+.

Workup

  1. extractionThen the mixture was extracted with ethyl acetate (50 ml×3)
  2. extractionextracted with ethyl acetate (50 ml×3)
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-101d7bb4f77946529eec5b7e88a74c39
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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