Acetic Acid → HCID 53804292, compound

HRID 1157011Notes

Reaction equation

HRID 1157011 reaction equation
[CH3:1][C:2]1[C:9]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[H-].[Na+].[C:21]([OH:24])(=[O:23])[CH3:22]>CS(C)=O.O1CCCC1>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]([C:9]2[C:2]([CH3:1])=[C:3]([CH:4]=[CH:4][CH2:3][CH2:2][CH2:9][CH2:8][CH2:22][C:21]([OH:24])=[O:23])[CH:6]=[CH:7][CH:8]=2)=[O:18])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 20534474HCID 20534474, compound

Product 1

HCID 53804292HCID 53804292, compound

Reagents, catalysts & solvents 1

HCID 21830753dimethylsulfoxide THFSolvent

Conditions

Temperature
2 °C

Procedure

A solution of 2.585 g of 2-methyl-3-(4-chlorobenzoyl)benzaldehyde and 5.49 g of ω-carbethoxyhexyl triphenyl phosphonium bromide in 25 ml of a 1:1 dimethylsulfoxidetetrahydrofuran mixture was added with stirring in 3 minutes to 520 mg of a 60% oil suspension of sodium hydride in 15 ml of a 1:1 dimethylsulfoxide-tetrahydrofuran mixture cooled to 2° C. and stirring was continued for 16 hours at 24° C. after the temperature had risen. The mixture was then cooled to 5° C. and 2 ml of acetic acid were added thereto. The solvents were removed and the residue was empasted with isopropyl ether and then filtered to remove insolubles. The filtrate was evaporated and the residue was saponified in a mixture of 50 ml of methanol and 15 ml of a 2 N sodium hydroxide solution at 80° C. for 1 hour. The methanol was removed and water was added. The mixture was extracted with ether and the aqueous phase was treated with activated carbon, filtered and acidified with concentrated hydrochloric acid. The oily residue was extracted with ether and the ether phase was washed with water, dried over magnesium sulfate, filtered and concentrated to dryness to obtain 2.98 g of 8-[3'-(4-chlorobenzoyl)-2'-methyl-phenyl]-oct-7-enoic acid with an Rf=0.35 (8:2 CH2Cl2 -acetone mixture).

Workup

  1. temperatureThe mixture was then cooled to 5° C.
  2. customThe solvents were removed
  3. filtrationfiltered
  4. customto remove insolubles
  5. customThe filtrate was evaporated
  6. additionthe residue was saponified in a mixture of 50 ml of methanol and 15 ml of a 2 N sodium hydroxide solution at 80° C. for 1 hour
  7. customThe methanol was removed
  8. additionwater was added
  9. extractionThe mixture was extracted with ether
  10. additionthe aqueous phase was treated with activated carbon
  11. filtrationfiltered
  12. extractionThe oily residue was extracted with ether
  13. washthe ether phase was washed with water
  14. dry with materialdried over magnesium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-18ed599c5eae401891559c5832e8485d
Source dataset
uspto-grants-1982_06
Patent number
US04337353

Reaction notes

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