4-hydroxymethyl-N-(2-hydroxyphenyl)-benzamide → HCID 22601331, compound

HRID 2308273Notes

Reaction equation

HRID 2308273 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 22601331HCID 22601331, compoundYield 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-aaff6d988f534eefa7694f17ec26a7cf
Source dataset
uspto-grants-2004_12
Patent number
US06835731B2

Reaction notes

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