Dimethylformamide → Ethyl 2-(3-nitrophenoxy)tetradecanoate

HRID 620697Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH2:11]([O:13][C:14](=[O:29])[CH:15](Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH3:12].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(O)(=O)C.O>[CH2:11]([O:13][C:14](=[O:29])[CH:15]([O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH3:12]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 250 g (1.79 mol) of m-nitrophenol, 602 g (1.79 mol) of Alphabromo-myristic acid ethyl ester, 248 g (1.79 mol) of potassium carbonate, and 1350 ml of dimethylformamide is heated to 80° C. for 3 h with stirring. The mixture is then poured out slowly into a mixture of 2300 ml of water and 250 ml of acetic acid. The product is extracted with dichloromethane. The solvent is removed by evaporation.

Workup

extractionThe product is extracted with dichloromethane
customThe solvent is removed by evaporation

Sources & evidence

ORD record: ord-8e1268a3ad914c10b3412d4df8d51779
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04822729

Reaction notes

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