1,9-Nonanediol → 2-(9-Hydroxynonyloxy)-6-nitrobenzonitrile

HRID 711919

Reaction equation

C1CCN2C(=NCCC2)CC1.CN(C)C(N(C)C)=N.[CH2:20]([OH:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29].[N+:31]([C:34]1[CH:41]=[CH:40][CH:39]=[C:38]([N+]([O-])=O)[C:35]=1[C:36]#[N:37])([O-:33])=[O:32]>>[OH:30][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:38]1[CH:39]=[CH:40][CH:41]=[C:34]([N+:31]([O-:33])=[O:32])[C:35]=1[C:36]#[N:37]

Participants

Reactant 4

HCID 198351,9-Nonanediol

HCID 664601,1,3,3-Tetramethylguanidine

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

HCID 520718Dinitrobenzonitrile

Product 1

HCID 667458442-(9-Hydroxynonyloxy)-6-nitrobenzonitrileYield 30.7%

Procedure

Prepared as in Example 274c (except DBU was replaced with 1,1,3,3-tetramethylguanidine) from 1,9-nonanediol and 2,6-dinitrobenzonitrile in 30.7% yield. MS 307 (MH+).

Sources & evidence

ORD record: ord-cb45c08645774286b14ae0252469b5ee
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181276B2

Linked notes

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