Acetic Acid → HCID 178496561, compound

HRID 1463749Notes

Reaction equation

HRID 1463749 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH2:15][CH2:16][CH:17]3OCC[O:18]3)[CH2:11][CH2:10]2)[CH2:5][CH2:4]1.O.C(O)(=O)C.C(=O)([O-])O.[Na+]>O1CCOCC1>[CH3:1][O:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH2:15][CH2:16][CH:17]=[O:18])[CH2:11][CH2:10]2)[CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 178496560HCID 178496560, compound

Product 1

HCID 178496561HCID 178496561, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

6.2 g of 2-[2-[trans-4-(trans-4-methoxycyclohexyl)-cyclohexyl]ethyl]-1,3-dioxolane were treated with 100 ml of water, 50 ml of glacial acetic acid and 20 ml of dioxan while gassing with nitrogen. The mixture was stirred at 100° C. (bath temperature) for 1.5 hours, then neutralized with dilute sodium hydrogen carbonate solution and extracted three times with diethyl ether. The combined ether phases were washed once with water and twice with dilute sodium hydrogen carbonate solution, dried over magnesium sulfate, filtered and evaporated. Recrystallization of the crude aldehyde obtained (4.34 g) from 150 ml of petroleum ether at -20° C. gave 2.8 g of 3-[trans-4-(trans-4-methoxycyclohexyl) cyclohexyl]propionaldehyde in a purity of 96%.

Workup

  1. extractionextracted three times with diethyl ether
  2. washThe combined ether phases were washed once with water and twice with dilute sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customRecrystallization of the crude aldehyde
  7. customobtained (4.34 g) from 150 ml of petroleum ether at -20° C.

Sources & evidence

ORD record
ord-63d5a43e12234dbf81422729e33f51c9
Source dataset
uspto-grants-1994_04
Patent number
US05302317

Reaction notes

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