Ethanol → HCID 12854007, compound

HRID 2166843Notes

Reaction equation

HRID 2166843 reaction equation
[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7].[CH2:23](O)[CH3:24].S(=O)(=O)(O)O>C(Cl)CCl>[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([C:14](=[O:22])[C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:23][CH3:24])=[O:7]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 128540042,3-Dichloro-4-(4-hydroxybenzoyl)phenoxyacetic acid

Product 1

HCID 12854007HCID 12854007, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

85.38 g. (0.25 mole) of 2,3-dichloro-4-(4'-hydroxybenzoyl)-phenoxyacetic acid, 34.5 g. (0.75 mole) of ethanol, and 100 ml. of ethylene dichloride, using 3.5 ml. of sulfuric acid as the catalyst were mixed and refluxed with stirring overnight according to the procedure of Clinton and Laskowski, J.A.C.S. 70 3135, 1948. The acid gradually went into solution. The reaction layer was cooled, separated and the organic layer washed successively with water, twice with KHCO3, solution and finally with water. The dried ethylene dichloride was evaporated to dryness to give an oil which solidified to give 86 g. crude ester on trituration with pentane and filtering: m.p. 127°-9° (93% yield). This material was used without further purification in subsequent experiments.

Workup

  1. temperaturerefluxed
  2. temperatureThe reaction layer was cooled
  3. customseparated
  4. washthe organic layer washed successively with water, twice with KHCO3, solution and finally with water
  5. customThe dried ethylene dichloride was evaporated to dryness
  6. customto give an oil which
  7. customto give 86 g
  8. filtrationcrude ester on trituration with pentane and filtering
  9. customThis material was used without further purification in subsequent experiments

Sources & evidence

ORD record
ord-18e20219043642dea75f2cd110eaebe6
Source dataset
uspto-grants-1983_06
Patent number
US04389416

Reaction notes

Loading…