1-Bromoeicosane → Hentriacontane
Reaction equation
Cl[C:2](Cl)(Cl)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].[CH2:34](Br)CCCCCCCCCCCCCCCCCCC.C([Mg]Br)=CCCCCCCCCC>>[CH3:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:34]Participants
Procedure
In accordance with (1--1) and (1-2) of Example 1, using eicosanyl bromide and undecenylmagnesium bromide as the raw material, a similar reaction was carried out to obtain hentriacontane as the intermediate product and then by another reaction 1,1,1-trichlorodotriacontane was obtained. One gram of the thus obtained, 1,1,1-trichlorodotriacontane dissolved in 6 ml of n-butyl alcohol was placed in a 50-ml conical flask and 1.4 ml of distilled water and 2.5 g of potassium hydroxide were added to the solution in the flask. The mixture was heated to a temperature of 60° C. to make reaction for 30 hours under agitation. Then, iced water was added to the reaction mixture to cool the mixture, and after neutralizing with an aqueous dilute hydrochloric acid, the separated precipitate was collected by filtration and dried to obtain 0.82 g of the product. After recrystallizing from benzene, 0.52 g of dotriacontanoic acid melting at 95.5° C. was obtained with a yield of 60%.
Workup
- customa similar reaction
Sources & evidence
- ORD record
- ord-b98e70a8d0a948bfaffe010890522330
- Source dataset
- uspto-grants-1981_10
- Patent number
- US04294770
Reaction notes
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