Dimethyl Sulfoxide → HCID 67823058, compound

HRID 1646829Notes

Reaction equation

HRID 1646829 reaction equation
CS(C)=O.[OH-].[Na+].[Br-].[C:8]([CH2:11][CH2:12][CH2:13][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:10])=[O:9].[CH3:33][C:34]1[CH2:35][C:36]([CH:46]([CH3:50])[CH2:47][CH:48]=O)([O:44][CH3:45])[C:37]([CH3:43])=[C:38]([CH3:42])[C:39]=1[O:40][CH3:41]>O.C1COCC1>[CH3:45][O:44][C:36]1([CH:46]([CH3:50])[CH2:47][CH:48]=[CH:13][CH2:12][CH2:11][C:8]([OH:10])=[O:9])[C:37]([CH3:43])=[C:38]([CH3:42])[C:39]([O:40][CH3:41])=[C:34]([CH3:33])[CH2:35]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 10717451(3-Carboxypropyl)(triphenyl)phosphanium bromideHCID 19088044HCID 19088044, compound

Product 1

HCID 67823058HCID 67823058, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

DMSO (30 ml) was added to sodium hydroxide (1 g, 24 mmole, 60% oil suspension was washed with hexane and dried under reduced pressure) under an atmosphere of argon, followed heating at 80° C. for 1 hour with stirring. After cooling, 3-carboxypropyltriphenyl phosphonium bromide (4.6 g, 11 mmole) was added to the solution, followed by stirring at room temperature. After stirring for 10 minutes, a THF solution (5 ml) of 3-(3,5,6-trimethyl-1,4-dimethoxyphenyl)butanal (2.7 g, 11 mmole) was added dropwise to the mixed solution. The reaction solution was stirred at room temperature for 2 hours, and water (50 ml) was added to it. The organic layer was washed with toluene (100 ml), and the water layer was adjusted to pH 4 with 2N hydrochloric acid, followed by extraction with IPE. The organic layer was washed with water, dried and concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluting solution: IPE) to give 7-(1,4-dimethoxy-3,5,6-trimethylphenyl)-4-octenoic acid (2.2 g, 68%). δ8.80 (1H,COOH), 5.38(2h,m), 3.63(3H,s), 3.60(3H,s), 3.25 (1H,s), 2.40(6H,m), 2.25(3H,s), 2.15(6H,s), 1.30(3H,d,7Hz)

Workup

  1. temperatureAfter cooling
  2. stirringby stirring at room temperature
  3. stirringAfter stirring for 10 minutes
  4. stirringThe reaction solution was stirred at room temperature for 2 hours
  5. washThe organic layer was washed with toluene (100 ml)
  6. extractionfollowed by extraction with IPE
  7. washThe organic layer was washed with water
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customthe crude product was purified by silica gel column chromatography (eluting solution: IPE)

Sources & evidence

ORD record
ord-9a1403e773204d909a278318cf2e063d
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

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