Sodium Hydroxide → HCID 12232950, compound

HRID 1439552Notes

Reaction equation

HRID 1439552 reaction equation
[CH2:1]([C:4]([C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:27])[C:22]2[S:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)(C(OCC)=O)[C:5]([O:7]CC)=[O:6])[CH:2]=[CH2:3].[OH-].[Na+]>>[C:22]1([C:21]([C:18]2[CH:19]=[CH:20][C:15]([CH:4]([CH2:1][CH:2]=[CH2:3])[C:5]([OH:7])=[O:6])=[CH:16][CH:17]=2)=[O:27])[S:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 12232936HCID 12232936, compound

Product 1

HCID 12232950HCID 12232950, compound

Procedure

A mixture of 20.3 parts of diethyl 2-allyl-2-[p-(2-thenoyl)phenyl]malonate and 150 parts of sodium hydroxide solution 5% is stirred and refluxed for 5 hours. The reaction mixture is cooled and washed twice with 80 parts of ether. The aqueous phase is separated and acidified with concentrated hydrochloric acid solution till strongly acid; an oil is separated which solidifies. The product is extracted with ether. The extract is washed with water, dried and evaporated. The oily residue solidifies on triturating in petroleumether. The solid product is filtered off and crystallized from 32 parts of acetonitrile at -20° C, yielding 2-[p-(2-thenoyl)phenyl]-4-pentenoic acid; mp. 117.1° C; also named p-(2-thenoyl)-α-allyl-phenylacetic acid.

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureThe reaction mixture is cooled
  3. washwashed twice with 80 parts of ether
  4. customThe aqueous phase is separated
  5. customan oil is separated which
  6. extractionThe product is extracted with ether
  7. washThe extract is washed with water
  8. customdried
  9. customevaporated
  10. customon triturating in petroleumether
  11. filtrationThe solid product is filtered off
  12. customcrystallized from 32 parts of acetonitrile at -20° C

Sources & evidence

ORD record
ord-367f7ee4f11440978f2df087c6cb7b4d
Source dataset
uspto-grants-1977_11
Patent number
US04060528

Reaction notes

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