Formamide → N-(3,5-di-tert-butyl-4-hydroxybenzyl)formamide

HRID 1044449Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+].[CH:22]([NH2:24])=[O:23]>O>[CH:22]([NH:24][CH2:8][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:12]([OH:13])=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:10]=1)=[O:23]

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 11.09 g (47 mmol) 3,5-di-tert.butyl-4-hydroxybenzaldehyde, 40 g ammonium formate and 40 mL formamide were stirred and heated to 170° C. for 30 minutes. The mixture was allowed to cool down to room temperature and treated with 100 mL water. The crude N-formyl-3,5-di-tert.butyl-4-hydroxybenzyl-amine precipitated from the mixture, was isolated by filtration, washed with water and dried. The crude N-formyl-3,5-di-tert.butyl-4-hydroxybenzyl-amine was recrystallized from toluene/heptane 1/1. 9.36 g (76%) of N-formyl-3,5-di-tert.butyl-4-hydroxybenzyl-amine was isolated (130-1° C.).

Workup

temperatureto cool down to room temperature
customThe crude N-formyl-3,5-di-tert.butyl-4-hydroxybenzyl-amine precipitated from the mixture
customwas isolated by filtration
washwashed with water
customdried
customThe crude N-formyl-3,5-di-tert.butyl-4-hydroxybenzyl-amine was recrystallized from toluene/heptane 1/1

Sources & evidence

ORD record: ord-d02e0455bca441a0a8fc662603b90468
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563624B2

Reaction notes

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