Benzaldehyde → 2,4-Di-tert-butyl-6-(dimethylaminophenyl-methyl)-phenol

HRID 1611729Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:24][NH:25][CH3:26]>>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH:16]([N:25]([CH3:26])[CH3:24])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 674Dimethylamine

HCID 73112,4-Di-tert-butylphenol

Product 1

HCID 111519612,4-Di-tert-butyl-6-(dimethylaminophenyl-methyl)-phenolYield 77%

Conditions

Temperature: 140 °C

Procedure

A mixture of 51.5 g (0.25 mol) of 2,4-di-tert-butylphenol, 26.5 g (0.25 mol) of benzaldehyde and 42.3 g (0.375 mol) of a 40% aqueous solution of dimethylamine is heated in a closed vessel at 140° C. for 10 hours, the internal pressure rising to 5 bar. After cooling to room temperature, the reaction mixture solidifies. Crystallisation of the residue from isopropanol yields 65.2 g (77%) of 2,4-di-tert-butyl-6-(dimethylamino-phenyl-methyl)-phenol, m.p. 120-123° C. (compound (202), Table 2). Molecular weight C23H33NO (339.52). Analysis, calculated: C 81.37; H 9.80; N, 4.13%. Analysis, found: C 81.25; H 9.86; N 4.00%. 1HNMR (300 MHz, CDCl3, ppm): 1.19 (s, 9H); 1.44 (s, 9H); 2.26 (s, 6H); 4.34 (s, 1H); 6.75 (d, 1H); 7.29 (m, 6H); 12.43 (s, 1H).

Workup

temperatureAfter cooling to room temperature
customCrystallisation of the residue from isopropanol

Sources & evidence

ORD record: ord-a12b7c254b6341f7abb7bf27dd283311
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06989446B2

Reaction notes

Loading…