Acetic Acid → 3-[Butyl(ethyl)amino]phenol

HRID 1590434Notes

Reaction equation

HRID 1590434 reaction equation
[C:1]([O-])(=O)[CH3:2].[Pb+2].[C:6]([O-])(=O)[CH3:7].[NH2:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1.[H][H].[CH:20](=O)[CH:21](C)C.C(=O)C.C(O)(=O)C>[Pt].CO>[CH2:20]([N:10]([C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)[CH2:6][CH2:7][CH2:1][CH3:2])[CH3:21]

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 177Acetaldehyde2×HCID 6561Isobutyraldehyde2×HCID 9317Lead diacetateHCID 115683-AminophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 197705013-[Butyl(ethyl)amino]phenol

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent3×

Procedure

3-(N-Ethyl-N-butylamino)phenol was synthesized by following the procedure of Examples 29 and 30. In a 500 cc-volume SUS-made autoclave equipped with a stirrer were charged 185.5 g of methanol, 1.6 g of a catalyst comprising 5% by weight of platinum supported on activated carbon, and 0.015 g of lead acetate, and the mixture was stirred at room temperature for one hour. Thereafter, 32.7 g (0.30 mole) of m-aminophenol was charged, the hydrogen pressure was maintained at 10 kg/cm2, and 47.6 g of a methanol solution containing isobutyraldehyde (isobutyraldehyde content: 0.33 mole) was continuously introduced over a period of 30 minutes at 40° C. After completion of the introduction of isobutyraldehyde, the mixture was maintained at the same temperature for an additional 1 hour, after which 41.1 g of a methanol solution containing 45% by weight of acetaldehyde (acetaldehyde content: 0 42 mole), and 0.20 g (0.0033 mole) of acetic acid were continuously introduced over a period of 30 minutes. After completion of the introduction of acetaldehyde, the mixture was maintained at the same temperature for an additional 70 minutes and allowed to cool. The filtrate obtained by removing the catalyst by filtration was analyzed by gas chromatography, liquid chromatography, and GPC. The results are shown in Table 12.

Workup

  1. customIn a 500 cc-volume SUS-made autoclave equipped with a stirrer
  2. additionwas continuously introduced over a period of 30 minutes at 40° C
  3. additionwere continuously introduced over a period of 30 minutes
  4. temperatureto cool
  5. customThe filtrate obtained
  6. customby removing the catalyst
  7. filtrationby filtration

Sources & evidence

ORD record
ord-b5e29da02cb94df4b3444152719d53ff
Source dataset
uspto-grants-1993_04
Patent number
US05202485

Reaction notes

Loading…