Water → HCID 178444465, compound

HRID 2254994Notes

Reaction equation

HRID 2254994 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][CH2:14][O: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]([CH2:32]O)[CH2:30][OH:31])[CH2:25][CH2:26][CH2:27][CH3:28].S(=O)(=O)(O)O.O>C1(C)C=CC=CC=1>[CH2:24]([C@@H:29]1[CH2:30][O:31][C@@H:20]([C:19]2[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH2:13][CH2:12][C@H:9]3[CH2:10][CH2:11][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8]3)=[CH:23][CH:22]=2)[O:21][CH2:32]1)[CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 1175092-Pentyl-1,3-propanediolHCID 178444467HCID 178444467, compound

Product 1

HCID 178444465HCID 178444465, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2.1 g of 4-[3-(trans-4-pentylcyclohexyl)-1-propyloxy]benzaldehyde and 1.2 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 2.5 hours, with the resulting water being distilled off simultaneously. Then, 4 drops of triethylamine were added to the reaction mixture. After cooling the mixture was washed with 20 ml of 1N sodium hydrogen carbonate solution and twice with 20 ml of water each time, dried over sodium sulfate, filtered and concentrated. Chromatography of the residue on silica gel with toluene gave 0.6 g of trans-5-pentyl-2-(4-[3-(trans-4-pentylcyciohexyl)-1-propyloxy]phenyl)-1,3-dioxane. M.p. (C-SB) 65° C. transition SB -N 73° C., cl.p (N-I) 128° C.

Workup

  1. temperatureThe mixture was heated
  2. distillationdistilled off simultaneously
  3. additionThen, 4 drops of triethylamine were added to the reaction mixture
  4. temperatureAfter cooling the mixture
  5. washwas washed with 20 ml of 1N sodium hydrogen carbonate solution and twice with 20 ml of water each time
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-92c44f29258640bda3d104c98171bdba
Source dataset
uspto-grants-1993_08
Patent number
US05238600

Reaction notes

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