3-Hydroxybenzaldehyde → 3-(Anilinomethyl)phenol

HRID 1497982Notes

Reaction equation

HRID 1497982 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[C:11]1([NH:10][CH2:5][C:4]2[CH:3]=[C:2]([OH:1])[CH:9]=[CH:8][CH:7]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 176Acetic AcidHCID 6115AnilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 213213663-(Anilinomethyl)phenolYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-hydroxybenzaldehyde (1.05 g, 8.6 mmol) and aniline (821 μL, 9.0 mmol) in dichloromethane (35 mL) was added acetic acid (516 μL, 9.0 mmol). The reaction mixture was stirred at room temperature for 24 hours. Sodium triacetoxyborohydride (4.55 g, 21.5 mmol) was added, and the reaction was stirred at room temperature for 24 hours. Water was added to quench the reaction and the mixture was diluted with dichloromethane. The organic layer was washed with brine, passed through a hydrophobic frit and the solvent was removed in vacuo to afford the title compound as a brown oil (1.7 g, quantitative yield).

Workup

  1. stirringthe reaction was stirred at room temperature for 24 hours
  2. customto quench
  3. customthe reaction
  4. washThe organic layer was washed with brine
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5abb60be551b40a7ad6689acef24dd8f
Source dataset
uspto-grants-2015_12
Patent number
US09199980B2

Reaction notes

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