3-Hydroxybenzaldehyde → 3-(Dimethylaminomethyl)phenol

HRID 624328Notes

Reaction equation

HRID 624328 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-fb8d2162ac9c4c14a6d8c52ea581c100
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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