Formaldehyde → HCID 66704338, compound

HRID 2261776Notes

Reaction equation

HRID 2261776 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 and the reaction is stirred overnight. The reaction 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 is stirred overnight
  2. concentrationThe reaction is concentrated under reduced pressure
  3. customthe residue is purified via chromatography

Sources & evidence

ORD record
ord-c44816b84a4b4554a7dbe76de92d1a6c
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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