3-Hydroxybenzaldehyde → 3-(Dimethylaminomethyl)phenol

HRID 1848806Notes

Reaction equation

HRID 1848806 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-df5af0ca9d194e2f9c958e27b101116e
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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