4-Pentenoic acid → HCID 86636726, compound

HRID 1691542Notes

Reaction equation

HRID 1691542 reaction equation
[CH2:1]([P:9]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]C(=O)CCCCP(CCCCCCCC)(CCCCCCCC)=O)=[O:24])([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].P([O-])(OCCCC)(OCCCC)=O.C([Mg]I)CCCCCCC.C(O)(=O)CCC=C>>[CH2:1]([P:9]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 4

HCID 611384-Pentenoic acidHCID 3790919Dibutyl phosphate anionHCID 86636727HCID 86636727, compoundHCID 178443580HCID 178443580, compound

Product 1

HCID 86636726HCID 86636726, compound

Procedure

In a similar vein, hybrid dispersing agents were designed for CdSe nanoparticles and in this case, phosphine oxide chain ends were required for interaction with the surface of the CdSe. Using an anhydride functionalization approach requires 5-(dioctylphosphoryl)pentanoic anhydride, 13, which was synthesized by initial alkylation of di-n-butyl phosphate, 14, with octylmagnesium iodide followed by reaction with 4-pentenoic acid using AlBN to give 5-(dioctylphosphoryl)pentanoic acid, 15, which was converted into the desired anhydride, 13, using DCC (See FIG. 9). The anhydride was then used to functionalize the chain ends of 9a to give the phosphine oxide functionalized dendritic-linear copolymer, 16 (See FIG. 10).

Workup

  1. additionIn a similar vein, hybrid dispersing agents

Sources & evidence

ORD record
ord-957e702899d74f0b989b9243c2392d4a
Source dataset
uspto-grants-2012_04
Patent number
US08153729B2

Reaction notes

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