Sulfuric Acid → HCID 178444438, compound

HRID 2226078Notes

Reaction equation

HRID 2226078 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][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]([CH2:12][CH2:13][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 178444445HCID 178444445, compound

Product 1

HCID 178444438HCID 178444438, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3 g of 4-[4-(trans-4-pentylcyclohexyl)-1-butyl]benzaldehyde and 1.7 g of 2-pentyl-1,3-propanediol in 50 ml of toluene was treated with 2 drops of 10% (vol.) sulfuric acid. The mixture was heated to boiling for 2 hours, whereby the resulting water was distilled off simultaneously. 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 sulfate, 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-[4-(trans-4-pentylcyclohexyl)-1-butyl]phenyl-1,3-dioxane with m.p. (C-N) 73° C. and clop. (N-Z) 106° C.

Workup

  1. temperatureThe mixture was heated
  2. distillationwhereby the resulting water was distilled off simultaneously
  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 sulfate
  7. filtrationfiltered
  8. concentrationsubsequently concentrated
  9. customChromatography of the residue on silica gel with toluene and recrystallization from acetone

Sources & evidence

ORD record
ord-bff2a50c41ad41fa89ec2d12f5259580
Source dataset
uspto-grants-1994_09
Patent number
US05346647

Reaction notes

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