3-Hydroxybenzaldehyde → 3-(Dimethylaminomethyl)phenol

HRID 1043059

Reaction equation

HRID 1043059 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-a87bbf9c63684d14a3aff343df0d7a24
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Linked notes

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