Ethanol → HCID 12854007, compound

HRID 1757959Notes

Reaction equation

HRID 1757959 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

An 85.38 g. (0.25 mole) portion 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 was 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-a4862225352a4b7d8ca04d4b57639282
Source dataset
uspto-grants-1983_02
Patent number
US04371546

Reaction notes

Loading…