Acetic Acid → Methyl 4-((3-((phenylamino)methyl)phenoxy)methyl)benzoate

HRID 520334Notes

Reaction equation

HRID 520334 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][CH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)=O.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[NH:21]([CH2:1][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][CH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 5049666Sodium triacetoxyborohydrideHCID 28825911Methyl 4-((3-formylphenoxy)methyl)benzoate

Product 1

HCID 86720705Methyl 4-((3-((phenylamino)methyl)phenoxy)methyl)benzoateYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of methyl 4-((3-formylphenoxy)methyl)benzoate (464 mg, 1.72 mmol) in anhydrous DCM (8 mL) was added aniline (0.63 mL, 6.87 mmol) followed by glacial acetic acid (0.46 mL, 6.87 mmol). The reaction was stirred at room temperature for 18 hours. Sodium triacetoxyborohydride (1.52 g, 6.87 mmol) was added and the reaction was stirred at room temperature for 2 hours. The mixture was diluted with DCM (100 mL). The organic layer was washed with 1 N HCl (3×30 mL) and saturated aqueous NaHCO3 (30 mL) and passed through a hydrophobic fit. The solvent was removed in vacuo to afford the title compound as an oil that solidifies on standing (380 mg, 64% yield).

Workup

  1. stirringthe reaction was stirred at room temperature for 2 hours
  2. washThe organic layer was washed with 1 N HCl (3×30 mL) and saturated aqueous NaHCO3 (30 mL)
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6b3f667027144974be333e5c74f978dc
Source dataset
uspto-grants-2016_05
Patent number
US09326976B2

Reaction notes

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