2,4,5-Trichlorophenol → Ethyl 5(2,4,5-trichlorophenoxy)-2-nitrobenzoate

HRID 358194

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[OH:10].[H-].[Na+].[CH2:13]([O:15][C:16](=[O:27])[C:17]1[CH:22]=[C:21](Cl)[CH:20]=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25])[CH3:14]>CC(N(C)C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[O:10][C:21]1[CH:20]=[CH:19][C:18]([N+:24]([O-:26])=[O:25])=[C:17]([CH:22]=1)[C:16]([O:15][CH2:13][CH3:14])=[O:27]

Participants

Conditions

Temperature: 120 °C

Procedure

2,4,5-Trichlorophenol (20 g) in dry dimethylacetamide (40 ml) was treated with sodium hydride (5.28 g of 50% dispersion in oil) in portions and the resulting mixture heated to 120° C. Ethyl-5-chloro-2-nitrobenzoate (16.5 g) was added in solution in dry dimethylacetamide (60 ml) and the mixture heated at 160° C. for ten hours. The solvent was removed and the residue washed with water and extracted with ether. The ether solution was extracted with ether. The ether solution was evaporated. The remaining oil solidified and was recrystallised from ethanol to give ethyl 5(2,4,5-trichlorophenoxy)-2-nitrobenzoate (10.9 g) with a melting point of 99°-102° C.

Workup

temperaturethe mixture heated at 160° C. for ten hours
customThe solvent was removed
washthe residue washed with water
extractionextracted with ether
extractionThe ether solution was extracted with ether
customThe ether solution was evaporated
customThe remaining oil solidified and was recrystallised from ethanol

Sources & evidence

ORD record: ord-61b2158dbd114476afce0389eb0a81b9
Source dataset: uspto-grants-1984_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04465508

Linked notes

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