Sodium Hydroxide → HCID 12232948, compound

HRID 258899Notes

Reaction equation

HRID 258899 reaction equation
[CH2:1]([C:3]([C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:26])[C:21]2[S:25][CH:24]=[CH:23][CH:22]=2)=[CH:16][CH:15]=1)(C(OCC)=O)[C:4]([O:6]CC)=[O:5])[CH3:2].[OH-].[Na+]>O>[C:21]1([C:20]([C:17]2[CH:18]=[CH:19][C:14]([CH:3]([CH2:1][CH3:2])[C:4]([OH:6])=[O:5])=[CH:15][CH:16]=2)=[O:26])[S:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12232934HCID 12232934, compound

Product 1

HCID 12232948HCID 12232948, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 16.8 parts of diethyl 2-ethyl-2-[p-(2-thenoyl)phenyl]malonate, 4 parts of sodium hydroxide and 80 parts of water is stirred and refluxed for 6 hours. The reaction mixture is poured onto water and the whole is extracted with ether. The aqueous phase is separated and acidified with hydrochloric acid solution: the product is separated as an oil which solidifies. It is extracted with ether. The extract is washed three times with water, dried, filtered and evaporated. The solid residue is crystallized from 24 parts of acetonitrile at room temperature, yielding 2-[p-(2-thenoyl)phenyl]butyric acid, also named p-(2-thenoyl)-α-ethyl-phenylacetic acid; mp. 122.8° C.

Workup

  1. temperaturerefluxed for 6 hours
  2. additionThe reaction mixture is poured onto water
  3. extractionthe whole is extracted with ether
  4. customThe aqueous phase is separated
  5. customthe product is separated as an oil which
  6. extractionIt is extracted with ether
  7. washThe extract is washed three times with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe solid residue is crystallized from 24 parts of acetonitrile at room temperature

Sources & evidence

ORD record
ord-1146639f09f3462784332d1b5c2d108b
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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