Water → HCID 178444446, compound

HRID 1590522Notes

Reaction equation

HRID 1590522 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9](/[CH:12]=[CH:13]/[CH2:14][CH2:15][C:16]2[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].CC(C)=[O:26].OS(O)(=O)=O.O=[Cr](=O)=O.O>CC(C)=O>[CH2:1]([C@H:6]1[CH2:7][CH2:8][C@H:9](/[CH:12]=[CH:13]/[CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([OH:26])=[O:21])=[CH:22][CH:23]=2)[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 131709961Jones' reagentHCID 178444444HCID 178444444, compound

Product 1

HCID 178444446HCID 178444446, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4 g of 4-[4E-(trans-4-pentylcyclohexyl)-3-butenyl]benzaldehyde (prepared according to Example 5) in 100 ml of acetone was treated dropwise with 10 ml of Jones' reagent. The mixture was stirred at room temperature for 1 hour and then poured into 100 ml of water. The precipitate which thereby resulted was filtered off, washed portionwise with water and dried in a vacuum. The crude product was recrystallized from ethanol and gave 2.5 g of pure 4-[4E-(trans-4-pentylcyclohexyl)-3-butenyl]benzoic acid.

Workup

  1. customThe precipitate which thereby resulted
  2. filtrationwas filtered off
  3. washwashed portionwise with water
  4. customdried in a vacuum
  5. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-220ee6855d8247cbae01a509de2b2065
Source dataset
uspto-grants-1993_04
Patent number
US05204018

Reaction notes

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