Sodium Iodide → HCID 86752382, compound

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].Br[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

Reactant 4

HCID 5238Sodium Iodide

HCID 11430Potassium Carbonate

HCID 76300Ethyl 4-bromobutyrate

HCID 1425504-Hydroxy-3-nitrobenzyl alcohol

Product 1

HCID 86752382HCID 86752382, compoundYield 86.6%

Procedure

4-Hydroxy-3-nitrobenzyl alcohol (1 g, 5.91 mmol) is treated with 1.44 g (7.39 mmol) of ethyl 4-bromobutyrate, 2.86 g (20.69 mmol) of potassium carbonate and a catalytic amount (88 mg 0.59 mmol) of sodium iodide as described in Preparation 3 to give 1.45 g of 4-[4-(hydroxymethyl)2-nitrophenoxy]butanoic acid, ethyl ester as a light yellow oil (86%). The 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (neat) 3400, 1730, 1710, 1630, 1580 cm-1 ; MS (CI) m/e 284 (M+H), 238; Analysis calculated for C13H17 O6N: C, 55.12; H, 6.05; found: C, 55.36; H, 6.03.