Water → HCID 178444469, compound

HRID 2254996Notes

Reaction equation

HRID 2254996 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][CH2:14][O: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[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([OH:26])=[O:21])=[CH:22][CH:23]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 131709961Jones' reagentHCID 178444467HCID 178444467, compound

Product 1

HCID 178444469HCID 178444469, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5 g of 4-[3-(trans-4-pentylcyclohexyl)-1-propyloxy]benzaldehyde 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 2.2 g of pure 4-[3-(trans-4-pentylcyclohexyl)-1-propyloxy]benzoic acid with m.p. (C-N) 204° C., cl.p. (N-I) 215° C.

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-053fdf880f6b4cf69f611515a0a31984
Source dataset
uspto-grants-1993_08
Patent number
US05238600

Reaction notes

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