3-Hydroxybenzaldehyde → 3-(Dimethylaminomethyl)phenol

HRID 573040

Reaction equation

HRID 573040 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:10][NH:11][CH3:12].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO>C1COCC1.C(Cl)Cl>[CH3:10][N:11]([CH2:5][C:4]1[CH:3]=[C:2]([OH:1])[CH:9]=[CH:8][CH:7]=1)[CH3:12]

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 674DimethylamineHCID 887MethanolHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 328963-(Dimethylaminomethyl)phenol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxybenzaldehyde (1.0 g), 2M dimethylamine in THF (5 mL), and sodium triacetoxyborohydride (2 g) in CH2Cl2 (10 mL) were stirred for 24 hours. The mixture was treated with methanol and chromatographed on silica gel with 2-25% ethyl acetate/hexanes.

Workup

  1. customchromatographed on silica gel with 2-25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d708a61eaf2640978e694ace5edbc94a
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Linked notes

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