1-Iodopropane → 5-Nitro-2-propyloxybenzaldehyde

HRID 500423Notes

Reaction equation

HRID 500423 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].I[CH2:14][CH2:15][CH3:16].COC(O)C1C=C([N+]([O-])=O)C=CC=1OC>>[N+:10]([C:7]1[CH:8]=[CH:9][C:2]([O:1][CH2:14][CH2:15][CH3:16])=[C:3]([CH:6]=1)[CH:4]=[O:5])([O-:12])=[O:11]

Participants

4

Reactant 3

HCID 336431-IodopropaneHCID 668085-NitrosalicylaldehydeHCID 210144602-Methoxy-5-nitrobenzaldehyde methyl hemiacetal

Product 1

HCID 219043575-Nitro-2-propyloxybenzaldehydeYield 72%

Procedure

This compound was prepared by the reaction of 2-hydroxy-5-nitrobenzaldehyde and 1-iodopropane using a similar procedure as described in the preparation of 2-methoxy-5-nitrobenzaldehyde methyl hemiacetal. Yield was 72%: MP (51-52° C.); 1H NMR (500 MHz, CDCl3) δ 10.46 (s, 1H), 8.68 (d, 1H, J=2.9 Hz), 8.39 (dd, 1H, J=2.7 and 9.1 Hz), 7.08 (d, 1H, J=9.1 Hz), 4.16 (t, 2H, J=6.2), 1.93 (m, 2H), 1.98 (t, 3H, J=7.37).

Workup

  1. customMP (51-52° C.)

Sources & evidence

ORD record
ord-36f9acd2cff74e33854ef2dedc68da57
Source dataset
uspto-grants-2010_08
Patent number
US07772216B2

Reaction notes

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