Methylpropanediol → 5-Methyl-2-(4-nitrobenzyl)-1,3,2-dioxaphosphorinan-2-oxide

HRID 1079311Notes

Reaction equation

[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH2:8][P:9](=[O:12])([OH:11])[OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:15][CH:16]([CH2:19]O)[CH2:17]O>>[CH3:15][CH:16]1[CH2:19][O:11][P:9](=[O:10])([CH2:8][C:7]2[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[O:12][CH2:17]1

Participants

Reactant 2

HCID 75103Methylpropanediol

HCID 5180708(4-Nitro-benzyl)-phosphonic acid

Product 1

HCID 189280815-Methyl-2-(4-nitrobenzyl)-1,3,2-dioxaphosphorinan-2-oxide

Procedure

With 4-nitrobenzylphosphonic acid and 2-methyl-1,3-propanediol, the same procedure as in Reference Example 11 was followed, to yield 5-methyl-2-(4-nitrobenzyl)-1,3,2-dioxaphosphorinane-2-oxide, which was then recrystallized from ethanol-hexane to yield colorless prisms having a melting point of170° to 171° C.

Sources & evidence

ORD record: ord-aa1a8444a4a5457ba77f15adbea9cd01
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05580863

Reaction notes

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