Dimethylamine → Diethyl ((3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)methyl)phosphonate

HRID 256756

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH2:16]=O.CNC.[P:21]([O:28]CC)([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24]>CN(C)C=O>[C:11]([C:7]1[CH:8]=[C:9]([CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])[CH2:16][P:21](=[O:28])([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 105 °C

Procedure

20.63 g (100 mmol) of 2,6-di-tert-butylphenol, 5.22 g (174 mmol) of paraformaldehyde, 6.1 g (45 mmol) of 33% ethanolic dimethylamine and 26 ml (=24.7 g) of N,N-dimethylformamide are heated at 50° C. under nitrogen for 1 hour in a sulfonation flask fitted with a reflux condenser and mechanical stirrer. 33.23 g (200 mmol) of triethyl phosphite are added to this mixture. It is heated under reflux at a reaction temperature of 105° C.; the conversion to the final product is 82% (HPLC). Working-up: extraction (water/methylcyclohexane) and recrystallization (methylcyclohexane). Yield: 23.0 g (65%), melting point 120° C., purity (HPLC): 98%.

Workup

customfitted with a reflux condenser and mechanical stirrer
temperatureIt is heated

Sources & evidence

ORD record: ord-c78b3fa2db894452937fd0352cb9630a
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05258540

Linked notes

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