Acetic Acid → 3-[Ethyl(2-methylpropyl)amino]phenol

Participants

Reaction Steps

3-(N-Ethyl-N-isobutylamino)phenol was synthesized by following the procedure of Examples 1 to 4. In a 500 cc-volume SUS-made autoclave equipped with a stirrer were charged 32.7 g (0.30 mole) of m-aminophenol, 185.5 g of methanol, and 1.6 g of a commercially available catalyst comprising 5% by weight of platinum supported on activated carbon containing 0.1 part by weight of lead per part by weight of platinum, and 47.6 g of a methanol solution containing 50% by weight of isobutyraldehyde (isobutyraldehyde content: 0.33 mole) was introduced over a period of 30 minutes at constant conditions of 40° C. and 10 kg/cm2G. After completion of the introduction of isobutyraldehyde, the mixture was maintained at the same temperature for an additional 60 minutes, 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 catalyst was removed by filtration, and the resulting filtrate was analyzed by gas chromatography, liquid chromatography, and GPC. The catalyst recovered was reused in the next reaction. The results are as shown in Table 7.

Provenance & Evidence