Chloroacetone → 2-Propanone, 1-(2-nitrophenoxy)-

HRID 1515069Notes

Reaction equation

CC1N(C(C(Cl)Cl)=O)[C:10]2C=CC=[CH:6][C:5]=2[O:4]C1.[N+:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[OH:26])([O-:19])=[O:18].ClCC(=O)C>>[N+:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH2:10][C:5](=[O:4])[CH3:6])([O-:19])=[O:18]

Participants

Reactant 3

HCID 6571Chloroacetone

HCID 69472-Nitrophenol

HCID 62306Benoxacor

Product 1

HCID 792392-Propanone, 1-(2-nitrophenoxy)-

Procedure

The preparation of benoxacor, a safener in the use of herbicides, is a three-stage process: in the first stage, o-nitrophenol is reacted with chloroacetone to give o-nitrophenoxyacetone; in the second stage, the compound is hydrogenated so as to obtain a benzoxazine, which is then acylated. This process is described in EP1283829.

Sources & evidence

ORD record: ord-c0eb509fbaae4029930285b12d1754dd
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222408B2

Reaction notes

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