Ethanol → Ethyl [2,3-dichloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)-phenoxy]acetate

HRID 1732178Notes

Reaction equation

HRID 1732178 reaction equation
[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([C:14]2[CH:19]([CH2:20][CH3:21])[CH2:18][CH2:17][C:16](=[O:22])[CH:15]=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>[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([C:14]2[CH:19]([CH2:20][CH3:21])[CH2:18][CH2:17][C:16](=[O:22])[CH:15]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:23][CH3:24])=[O:7]

Participants

4

Reactant 2

HCID 702EthanolHCID 10759778[2,3-Dichloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid

Product 1

HCID 13749111Ethyl [2,3-dichloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)-phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A stirred solution of [2,3-dichloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid (3.43 g, 0.01 mole) in ethanol (50 ml) containing sulfuric acid (4 drops) was heated at reflux for 4 hours. The ethanol was evaporated at reduced pressure, the residue dissolved in ether, washed with dilute sodium hydroxide, water, dried over magnesium sulfate and evaporated in vacuo to give 3.31 g of ethyl [2,3-dichloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)-phenoxy]acetate which melted at 110°-112° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe ethanol was evaporated at reduced pressure
  4. dissolutionthe residue dissolved in ether
  5. washwashed with dilute sodium hydroxide, water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-27a63db16c5442c7a29ebdb35af297ee
Source dataset
uspto-grants-1986_11
Patent number
US04625047

Reaction notes

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