Acetyl chloride → 3-(2-Cyano-3-nitrophenoxy)-2-methylpropyl acetate

Reaction equation

[OH:1][CH2:2][CH:3]([CH3:17])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[C:7]=1[C:8]#[N:9].[C:18](Cl)(=[O:20])[CH3:19]>>[C:18]([O:1][CH2:2][CH:3]([CH3:17])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[C:7]=1[C:8]#[N:9])(=[O:20])[CH3:19]

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 673988582-(3-Hydroxy-2-methylpropoxy)-6-nitrobenzonitrile

Product 1

HCID 674005323-(2-Cyano-3-nitrophenoxy)-2-methylpropyl acetateYield 41%

Procedure

Prepared as in Example 231c from 2-(3-hydroxy-2-methylpropoxy)-6-nitrobenzonitrile (Example 237d) and acetyl chloride in 41% yield. 1H NMR (400 MHz, DMSO-d6) δ 1.04 (d, J=6.8 Hz, 3H), 2.00 (s, 3H), 2.28-2.33 (m, 1H), 4.05-4.08 (m, 2H), 4.18 (d, J=6.0 Hz, 2H), 7.71-7.73 (m, 1H), 7.86-7.92 (m, 2H).

Sources & evidence

ORD record: ord-0d3720b2ebeb4cc593d0fa7afd13b083
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633186B2

Reaction notes

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