4-Methoxyphenol → Methyl 3,5-dinitro-4-(4-methoxyphenoxy)-benzoate

HRID 2303568

Reaction equation

[OH-].[K+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.Cl[C:13]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[N+:26]([O-:28])=[O:27]>O>[N+:26]([C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([N+:23]([O-:25])=[O:24])[C:13]=1[O:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=1)[C:17]([O:19][CH3:20])=[O:18])([O-:28])=[O:27]

Participants

Conditions

Temperature: 150 °C

Procedure

To a 100 mL round-bottomed flask containing potassium hydroxide (4.7 g; 82.0 mmol) dissolved in water (20 mL) was successively added 4-methoxyphenol (10.0 g; 80.6 mmol) and methyl 4-chloro-3,5-dinitrobenzoate (20.2 g; 77.5 mmol). The flask was fitted with a reflux condenser and the reaction heated at 150° C. (oil bath) for 3 hours. After cooling to room temp, the reaction mixture was transferred to a large mortar and triturated with cold 2N NaOH (100 mL) to remove unreacted phenol. The solid was collected by filtration and air-dried to give 21.5 g of crude product. Crystallization from absolute ethanol gave 17.7 g (65.6%) of pure methyl 3,5-dinitro-4-(4-methoxyphenoxy)benzoate as light yellow needles. 300 MHz 1H NMR (CDCl3) d 3.77 (s, 3H, OCH3), 4.02 (s, 3H, OCH3), 6.82 (m, 4H, ArH), 8.70 (s, 2H, ArH).

Workup

customThe flask was fitted with a reflux condenser
temperatureAfter cooling to room temp
customtriturated with cold 2N NaOH (100 mL)
customto remove unreacted phenol
filtrationThe solid was collected by filtration
customair-dried
customto give 21.5 g of crude product
customCrystallization from absolute ethanol

Sources & evidence

ORD record: ord-da8fa76c1557484d9473076d8e04bb11
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06433012B1

Linked notes

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