O-Cresol → HCID 14519867, compound

HRID 1198619Notes

Reaction equation

HRID 1198619 reaction equation
Cl[C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19].COCCOCCN(CCOCCOC)CCOCCOC>O1CCOCC1.Cl[Cu]>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([O:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH3:12])[CH:10]=1

Participants

6

Reactant 3

HCID 335O-CresolHCID 57872,4-Dichlorobenzoic AcidHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-

Product 1

HCID 14519867HCID 14519867, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of the sodium salts of 2,4-dichlorobenzoic acid (V: X=Cl, R1 =4-Cl) (27.7 g, 130 mmol) and 2-methylphenol (III: R3 =H) (18.9 g, 145 mmol) were dissolved in dry dioxan (300 mL). CuCl (1.3 g, 13 mmol) and tris-[2-(2-methoxyethoxy)ethyl]amine (TDA-1) (4.2 g, 13 mmol) were added, and the mixture was heated at reflux under N2 for 8 hours. Excess solvent was evaporated under reduced pressure, and the residue was diluted with water and filtered. The filtrate was acidified with 2N HCl, and the resulting precipitate was collected, washed well with water and dried to yield 4-chloro-2-(2-methylphenoxy) benzoic acid (IV: R1 =4-Cl, R3 =H) (27 g, 79%), which was suitable for the next step. A sample was crystallized from aqueous MeOH as prisms, mp 158°-159° C. Anal. (C14H11ClO3), C,H,Cl.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux under N2 for 8 hours
  3. customExcess solvent was evaporated under reduced pressure
  4. additionthe residue was diluted with water
  5. filtrationfiltered
  6. customthe resulting precipitate was collected
  7. washwashed well with water
  8. customdried

Sources & evidence

ORD record
ord-8a34dba1aeed439e8254e1a0d78d0625
Source dataset
uspto-grants-1994_01
Patent number
US05281620

Reaction notes

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