Sulfuric Acid → HCID 178444437, compound

HRID 1590521Notes

Reaction equation

HRID 1590521 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].[CH2:24]([CH:29](CO)[CH2:30][OH:31])CCCC.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[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]([CH:20]3[O:31][CH2:30][CH2:29][CH2:24][O:21]3)=[CH:22][CH:23]=2)[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 1175092-Pentyl-1,3-propanediolHCID 178444444HCID 178444444, compound

Product 1

HCID 178444437HCID 178444437, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

a solution of 3 g of 4-[4E-(trans-4-pentylcyclohexyl)-3-butenyl]benzaldehyde and 1.7 g of 2-pentyl-1,3-propanediol in 50 ml of toluene was treated with 2 drops of 10% (vol.) sulphuric acid. The mixture was heated to boiling for 2 hours, whereby the resulting water was simultaneously distilled off. Then, 4 drops of triethylamine were added to the reaction mixture. After cooling the mixture was washed with 50 ml of 1N sodium hydrogen carbonate solution and twice with 50 ml of water each time, dried over magnesium sulphate, filtered and subsequently concentrated. Chromatography of the residue on silica gel with toluene and recrystallization from acetone gave 1.2 g of trans-5-pentyl-2-(4-[4E-(trans-4-pentylcyclohexyl)-3-butenyl]phenyl-1,3-dioxane.

Workup

  1. temperatureThe mixture was heated
  2. distillationwhereby the resulting water was simultaneously distilled off
  3. additionThen, 4 drops of triethylamine were added to the reaction mixture
  4. temperatureAfter cooling the mixture
  5. washwas washed with 50 ml of 1N sodium hydrogen carbonate solution and twice with 50 ml of water each time
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationsubsequently concentrated
  9. customChromatography of the residue on silica gel with toluene and recrystallization from acetone

Sources & evidence

ORD record
ord-21c92afbc41a4c208c3b3f3c9de96ad3
Source dataset
uspto-grants-1993_04
Patent number
US05204018

Reaction notes

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