Water → HCID 178448069, compound

HRID 266653Notes

Reaction equation

HRID 266653 reaction equation
[H-].[Na+].[CH2:3]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C@H:12]2[CH2:17][CH2:16][C@H:15](O)[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:4][CH3:5].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1.[OH2:29]>CN(C)C=O>[CH2:3]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH:25]([O:29][CH:25]([C@H:15]3[CH2:16][CH2:17][C@H:12]([C@H:9]4[CH2:10][CH2:11][C@H:6]([CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8]4)[CH2:13][CH2:14]3)[C:24]3[CH:27]=[CH:28][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)[C:24]3[CH:27]=[CH:28][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 178448075HCID 178448075, compound

Product 1

HCID 178448069HCID 178448069, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 0.6 g of sodium hydride (purity 60%) was added 30 ml of anhydrous N,N-dimethylformamide. While stirring sufficiently, to the solution was added a solution of 3.36 g of trans-4-(trans-4-propylcyclohexyl)cyclohexanol dissolved in 10 ml of anhydrous N,N-dimethylformamide. This mixture was continued to stirring at 50° C. for one hour and then 2.8 g of 4-methoxybenzyl chloride was added thereto, and the mixture was stirred and reacted at the same temperature for 3 hours with stirring. After completion of the reaction, 100 ml of water was added to the reaction mixture, the mixture was extracted with toluene, washed with a saturated NaCl aqua, dried and the solvent was removed under reduced pressure. The residue was purified by silica gel column to obtain 1.0 g of the targeted trans-4-(trans-4-propylcyclohexyl)cyclohexyl-4-methoxybenzyl ether.

Workup

  1. stirringto stirring at 50° C. for one hour
  2. stirringthe mixture was stirred
  3. customreacted at the same temperature for 3 hours
  4. stirringwith stirring
  5. additionwas added to the reaction mixture
  6. extractionthe mixture was extracted with toluene
  7. washwashed with a saturated NaCl aqua
  8. customdried
  9. customthe solvent was removed under reduced pressure
  10. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-ec4c507ea5d148a283236f81b0bac551
Source dataset
uspto-grants-1997_07
Patent number
US05651919

Reaction notes

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