Phenol → Methyl 4-(2-methoxy-2-oxoethoxy)-3-nitrobenzoate

HRID 1184427Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C1(O)C=CC=CC=1.Br[CH2:23][C:24]([O:26][CH3:27])=[O:25]>>[CH3:27][O:26][C:24](=[O:25])[CH2:23][O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

Reactant 3

HCID 996Phenol

HCID 60984Methyl bromoacetate

HCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl ester

Product 1

HCID 17368159Methyl 4-(2-methoxy-2-oxoethoxy)-3-nitrobenzoate

Procedure

Using methyl 4-hydroxy-3-nitrobenzoate as the phenol and methyl 2-bromoacetate as the alkylating agent in the general procedure for alkylation of substituted-2-nitrophenols gives a light yellow solid: 1H NMR (DMSO-d6, 400 MHz): δ ppm 8.39 (d, J=2.0 Hz, 1H), 8.15 (dd, J=8.8, 2.3 Hz, 1H), 7.44 (d, J=8.8 Hz, 1H), 5.16 (s, 2H), 3.87 (s, 3H), 3.71 (s, 3H). ESI-MS: m/z 270.1 (M+H)+.

Workup

customgives a light yellow solid

Sources & evidence

ORD record: ord-126e50977449480c9852dc7dd79a2a9d
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669249B2

Reaction notes

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