Formic Acid → N-(4-hydroxy-2,3,6-trimethylphenyl)formamide

HRID 1493058Notes

Reaction equation

HRID 1493058 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([CH3:10])[C:3]=1[CH3:11].[CH:12](O)=[O:13]>>[CH:12]([NH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([CH3:10])[C:3]=1[CH3:11])=[O:13]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 111055374-Amino-2,3,5-trimethylphenol

Product 1

HCID 21961295N-(4-hydroxy-2,3,6-trimethylphenyl)formamideYield 72.5%

Procedure

4-Amino-2,3,5-trimethylphenol (100 g, 662 mmol) was dissolved in formic acid (500 ml). The mixture was heated under reflux for 36 hours. The reaction mixture was poured into ice-cold water. The precipitated crystals were filtered, washed with water and dried. The crude crystals obtained were recrystallized from ethanol to obtain the desired compound (85.9 g, yield: 72.5%), m.p. 219°-220° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 36 hours
  3. additionThe reaction mixture was poured into ice-cold water
  4. filtrationThe precipitated crystals were filtered
  5. washwashed with water
  6. customdried
  7. customThe crude crystals obtained
  8. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-4b7eaafb21d74fdf9ba545b50222efcc
Source dataset
uspto-grants-1994_12
Patent number
US05376681

Reaction notes

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