2,4,5-Trichlorophenol → HCID 12952183, compound

HRID 1659451Notes

Reaction equation

HRID 1659451 reaction equation
[C:1]([OH:15])(=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[C:20]([Cl:24])=[CH:19][C:18]=1O.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:1]([O:15][C:18]1[CH:19]=[C:20]([Cl:24])[C:21]([Cl:23])=[CH:22][C:17]=1[Cl:16])(=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 72712,4,5-TrichlorophenolHCID 10868DicyclohexylcarbodiimideHCID 12530Tridecanoic acid

Product 1

HCID 12952183HCID 12952183, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of n-tridecanoic acid (Sigma Chemical Co.) (12.5 g), 2,4,5-trichlorophenol (11.5 g), and N,N'-dicyclohexylcarbodiimide (12.0 g) in methylene chloride (650 ml) is stirred at room temperature for 16 hours. The reaction mixture is then filtered and dried in vacuo to give 2,4,5-trichlorophenyl n-tridecanoate (22 g). The material is purified by column chromatography over silica gel (Woelm) using toluene as the eluent. Fractions are monitored by TLC using a shortwave UV light for detection. Fractions containing the purified product are pooled and concentrated in vacuo to dryness.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-52aab54848854bd58291f1e1fdbd0b67
Source dataset
uspto-grants-1981_12
Patent number
US04304716

Reaction notes

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