Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 54091266, compound

HRID 1157010Notes

Reaction equation

HRID 1157010 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([C:8]2[C:9]([CH3:19])=[C:10]([CH2:14][CH2:15][CH2:16][CH:17]=O)[CH:11]=[CH:12][CH:13]=2)=O)=[CH:4][CH:3]=1.[C:22]([CH:27]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:24]CC)=[O:23]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:8]2[C:9]([CH3:19])=[C:10]([CH2:14][CH2:15][CH2:16][CH:17]=[CH:27][C:22]([OH:24])=[O:23])[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 20534478HCID 20534478, compound

Product 1

HCID 54091266HCID 54091266, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4.5 g of the said butyraldehyde and 5.48 g of carbethoxy methylene triphenyl phosphorane in 100 ml of toluene was refluxed under an inert atmosphere with stirring for 17 hours and the toluene was then evaporated. The residue was saponified with 30 ml of 2 N sodium hydroxide and 50 ml of methanol at 75°-80° C. and the methanol was then removed. Water was added to the mixture which was then washed with ether containing 20% of methylene chloride, was treated with activated carbon and filtered. The filtrate was acidified with concentrated hydrochloric acid and was extracted with ether. The ether extracts were treated with activated carbon, filtered and evaporated to dryness. The residue was chromatographed over silica and eluted with a 95:5 methylene chloride-methanol mixture. The product was crystallized from isopropyl ether to obtain 2.015 g of 6-[3'-(4-chlorobenzyl)-2'-methylphenyl]-hex-2-enoic acid melting at 115° C.

Workup

  1. temperaturewas refluxed under an inert atmosphere
  2. customthe toluene was then evaporated
  3. customwas saponified with 30 ml of 2 N sodium hydroxide and 50 ml of methanol at 75°-80° C.
  4. customthe methanol was then removed
  5. additionWater was added to the mixture which
  6. washwas then washed with ether containing 20% of methylene chloride
  7. additionwas treated with activated carbon
  8. filtrationfiltered
  9. extractionwas extracted with ether
  10. additionThe ether extracts were treated with activated carbon
  11. filtrationfiltered
  12. customevaporated to dryness
  13. customThe residue was chromatographed over silica
  14. washeluted with a 95:5 methylene chloride-methanol mixture
  15. customThe product was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-8e508623088742bca8c90c775d9094b3
Source dataset
uspto-grants-1982_06
Patent number
US04337353

Reaction notes

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