(2,4-Dichlorophenoxy)Acetic Acid → HCID 54145863, compound

HRID 372345Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([O:8][C:9](=[O:13])[NH:10][CH2:11]Cl)[CH:5]=[CH:6][CH:7]=1.[Cl:14][C:15]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:16]=1[O:17][CH2:18][C:19]([OH:21])=[O:20].C(N(CC)CC)C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:9]([NH:10][CH2:11][O:21][C:19](=[O:20])[CH2:18][O:17][C:16]1[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:15]=1[Cl:14])=[O:13]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 220.1 g (1 mole) of N-chloromethylcarbamic acid 3-chlorophenyl ester in 1 liter of anhydrous ethyl acetate was added dropwise at 0° to 10° C to a mixture of 221 g (1 mole) of 2,4-dichlorophenoxyacetic acid and 111.3 g (1.1 moles) of triethylamine in 2 liters of ethyl acetate. The mixture was stirred for a further 15 hours at 20° C and was cooled to 5° C, and the triethylammonium chloride which had precipitated was filtered off. The filtrate was washed neutral with water and was concentrated in vacuo by distilling off the solvent. The solid residue was recrystallised from ether. 290 g (71.8% of theory) of 2-(2,4-dichlorophenoxy)-acetic acid 3-chlorophenoxycarbonylaminomethyl ester were obtained in the form of white crystals of melting point 110° C.

Workup

temperaturewas cooled to 5° C
customthe triethylammonium chloride which had precipitated
filtrationwas filtered off
washThe filtrate was washed neutral with water
concentrationwas concentrated in vacuo
distillationby distilling off the solvent
customThe solid residue was recrystallised from ether

Sources & evidence

ORD record: ord-27effa9f695f4e52b343acd12879f16a
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04090862

Reaction notes

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