Formaldehyde → HCID 66704338, compound

HRID 424794Notes

Reaction equation

HRID 424794 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[CH3:10][O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][CH:14]=1.[B][B][B][B][B][B][B][B][B][B].[CH2:32]=O>CO>[CH3:10][O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:1]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=2[CH3:9])[CH3:32])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 15294Methyl 4-FormylbenzoateHCID 178194-Amino-m-cresolHCID 178419135HCID 178419135, compound2×

Product 1

HCID 66704338HCID 66704338, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ambient temperature solution of 4-amino-3-methyl-phenol (1.0 g, 8.12 mmol) in MeOH (77 mL) is added 4-formyl-benzoic acid methyl ester (1.47 g, 8.93 mmol) and decaborane (329 mg, 2.68 mmol). The reaction is stirred at room temperature. After 2 h, formaldehyde (1.23 mL, 16.93 mmol, 37% in water) and decaborane (329 mg, 2.68 mmol) are added to the reaction. The reaction mixture is stirred overnight. The reaction mixture is concentrated under reduced pressure and the residue is purified via chromatography to yield the title compound (2.07 g, 90%). LC-ES/MS m/e 286.2 (M+1).

Workup

  1. stirringThe reaction mixture is stirred overnight
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customthe residue is purified via chromatography

Sources & evidence

ORD record
ord-c546d41982c14b7daaba88a92f8a7639
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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