Water → HCID 178448012, compound

HRID 1419659Notes

Reaction equation

HRID 1419659 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]3[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[C:18]([F:25])[CH:17]=3)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C@H:10]2[CH2:11][CH2:12][C@H:13]([C:16]3[CH:24]=[CH:23][C:19]([CH2:20][OH:21])=[C:18]([F:25])[CH:17]=3)[CH2:14][CH2:15]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178448015HCID 178448015, compound

Product 1

HCID 178448012HCID 178448012, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

7.8 g of 4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]-2-fluorobenzoic acid are added to a suspension of 4.5 g of lithium aluminium hydride in 150 ml of dry ether and the mixture is stirred under reflux for 23 hrs. The suspension is cooled to 0° C., treated cautiously with 40 ml of water and then with 150 ml of 3N sulfuric acid, extracted with ether and the organic phase is dried over sodium sulfate, filtered and the filtrate is evaporated. Chromatography of the residue on silica gel with methylene chloride/acetone (95:5) gives 4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]-2-fluorobenzyl alcohol.

Workup

  1. temperatureunder reflux for 23 hrs
  2. extractionwith 150 ml of 3N sulfuric acid, extracted with ether
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-c0324d52de1b4e16847951354e377389
Source dataset
uspto-grants-1999_03
Patent number
US05888423

Reaction notes

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