Sodium Hydroxide → {2-Nitro-5-[(undec-10-en-1-yl)oxy]phenyl}methanol

HRID 964868

Reaction equation

HRID 964868 reaction equation
[SiH4].[OH:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:10]=1)[CH2:8][OH:9].[OH-].[Na+].[C:16](Br)(=O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH2:26]>[Br-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1>[N+:11]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=[CH2:16])=[CH:10][C:7]=1[CH2:8][OH:9])([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 23953SilaneHCID 1089463-(Hydroxymethyl)-4-nitrophenolHCID 21705948Undecylenic bromide

Product 1

HCID 19074081{2-Nitro-5-[(undec-10-en-1-yl)oxy]phenyl}methanol

Reagents, catalysts & solvents 1

HCID 2724282Benzenemethanaminium, N,N,N-tributyl-, bromideCatalyst

Procedure

Synthesis of a o-nitrobenzyl PEG-silane of the above formula wherein R3 is H and m=11 was achieved in three steps. First, 5-hydroxy-2-nitrobenzyl alcohol I in 0.3 NaOH was refluxed for four days with undecylenic bromide II (dissolved in CH2Cl2) in the presence of benzyltributylammonium bromide to form 2-nitro-5-(10-undecenyloxy)phenylmethanol III according to the following reaction scheme: ##STR6##

Sources & evidence

ORD record
ord-4e4e5ae11cbe458e8e3a31c676e798a5
Source dataset
uspto-grants-1998_06
Patent number
US05773308

Linked notes

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