Ethanol → HCID 13290000, compound

HRID 370944Notes

Reaction equation

HRID 370944 reaction equation
[Cl:1][C:2]1[C:3]([O:12][CH2:13][C:14]([O-:16])=[O:15])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[Cl:11].[OH-].[K+].C(O)C>O>[Cl:1][C:2]1[C:3]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[Cl:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 20197873HCID 20197873, compound

Product 1

HCID 13290000HCID 13290000, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7.5 g of ethyl[(6,7-dichlorobenzo[b]thien-5-yl oxy]acetate, 15 g of potassium hydroxide pellets, 125 ml of ethanol and 125 ml of water is refluxed for 1 hour. Ethanol is removed under reduced pressure at 60° and the aqueous suspension is acidified with conc hydrochloric acid. The slurry is stirred at room temperature for 30 min. and extracted with ether (3×250 ml-portions). The combined ether extracts are washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to give an off-white crystalline mass. Recrystallization of the crude product from acetone-cyclohexane gives 6.5 g of [(6,7-dichlorobenzo[b]thien-5-yl)oxy]acetic acid as an off-white powder, mp 166°-167°.

Workup

  1. temperatureis refluxed for 1 hour
  2. customEthanol is removed under reduced pressure at 60°
  3. extractionextracted with ether (3×250 ml-portions)
  4. washThe combined ether extracts are washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an off-white crystalline mass
  8. customRecrystallization of the crude product from acetone-cyclohexane

Sources & evidence

ORD record
ord-a9aa24cbb6e744729381789b8acc3568
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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