Phenol → HCID 86664209, compound

HRID 1184445Notes

Reaction equation

HRID 1184445 reaction equation
[OH:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:13].C1(O)C=CC=CC=1.[CH3:21][O:22][C:23](=[O:27])[CH:24](Br)[CH3:25]>>[CH:6]([C:5]1[CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]([O:1][CH:24]([CH3:25])[C:23]([O:22][CH3:21])=[O:27])=[C:3]([CH3:13])[CH:4]=1)=[O:7]

Participants

4

Reactant 3

HCID 996PhenolHCID 95576Methyl 2-bromopropionateHCID 14512993HCID 14512993, compound

Product 1

HCID 86664209HCID 86664209, compound

Procedure

Using 4-hydroxy-3-methyl-5-nitrobenzaldehyde as the phenol and methyl-2-bromopropanoate as the alkylating agent in the general procedure of alkylation of substituted 2-nitrophenols gives a light tan solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.49-1.56 (m, 3H) 2.42 (s, 3H) 3.62 (s, 3H) 4.82 (q, J=6.82 Hz, 1H) 8.10 (d, J=1.52 Hz, 1H) 8.29 (d, J=1.52 Hz, 1H) 9.98 (s, 1H). ESI-MS: m/z 268.2 (M+H)+.

Workup

  1. customgives a light tan solid

Sources & evidence

ORD record
ord-17845d4ea4ee405eada5a1427c8a9c52
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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