4-hydroxymethyl-N-(2-hydroxyphenyl)-benzamide → 4-formyl-N-(2-hydroxyphenyl)-benzamide

HRID 970894Notes

Reaction equation

HRID 970894 reaction equation
[OH:1][CH2:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])=[O:8])=[CH:5][CH:4]=1>C(Cl)Cl.C1COCC1.O=[Mn]=O>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])=[O:8])=[CH:17][CH:18]=1)=[O:1]

Participants

5

Reactant 1

HCID 226013794-hydroxymethyl-N-(2-hydroxyphenyl)-benzamide

Product 1

HCID 226013314-formyl-N-(2-hydroxyphenyl)-benzamideYield 10%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Hydroxymethyl-N-(2-hydroxyphenyl)-benzamide from above (0.56 g, 2.3 mmol) was dissolved in CH2Cl2 (12 mL) and THF (12 mL), treated with activated MnO2 (2.0 g, 23 mmol) and stirred at room temperature overnight. The mixture was filtered through celite, the cake washed with CH2Cl2 and the solvent from the eluent removed under reduced pressure. Purification of the crude by column chromatography on silica gel (5% MeOH/CH2Cl2) gave 4-formyl-N-(2-hydroxyphenyl)-benzamide (0.05 g, 10%). 1H NMR (CDCl3) δ 6.95 (t, 1H, J=7.8 Hz), 7.05 (d, 1H, J=7.8 Hz), 7.16 (t, 1H, J=7.8 Hz), 7.42 (d, 1H, J=7.8 Hz), 8.04 (m, 5H), 8.33 (br, 1H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe cake washed with CH2Cl2
  3. customthe solvent from the eluent removed under reduced pressure
  4. customPurification of the crude by column chromatography on silica gel (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-de8896a2c5f5491fb52567e4eb1ca5bb
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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