Sodium Hydroxide → HCID 13290053, compound

HRID 652675Notes

Reaction equation

HRID 652675 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[C:21]([Cl:22])=[C:20]([Cl:23])[C:10]2[S:11][C:12]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:13][C:9]=2[CH:8]=1)C.[OH-].[Na+]>C(O)C>[Cl:22][C:21]1[C:7]([O:6][CH2:5][C:4]([OH:24])=[O:3])=[CH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[S:11][C:10]=2[C:20]=1[Cl:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13290052HCID 13290052, compound

Product 1

HCID 13290053HCID 13290053, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 11.8 g of ethyl[(6,7-dichloro-2-cyclohexylbenzo[b]thien-5-yl)oxy]acetate, 250 ml of 20% sodium hydroxide and 250 ml of 95% ethanol is refluxed for 2 hrs. and allowed to cool. The solvent is removed. The residue is stirred in 350 ml of 6N hydrochloric acid for 2 hrs. The mixture is filtered and the solid is air-dried, taken up in ether and redried over anhydrous magnesium sulfate and filtered. Recrystallization of the residue from acetone-hexane gives 9.0 g of [(6,7-dichloro-2-cyclohexylbenzo[b]thien-5-yl)oxy]acetic acid, mp 167°-167.5°.

Workup

  1. temperatureis refluxed for 2 hrs
  2. temperatureto cool
  3. customThe solvent is removed
  4. filtrationThe mixture is filtered
  5. customthe solid is air-dried
  6. dry with materialredried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customRecrystallization of the residue from acetone-hexane

Sources & evidence

ORD record
ord-628fd0c87ce64e7d9114c84e9848a2da
Source dataset
uspto-grants-1987_06
Patent number
US04672138

Reaction notes

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