Sulfuric Acid → HCID 178448155, compound

HRID 1109687Notes

Reaction equation

HRID 1109687 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH:15]=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[CH:17](/[CH:20]([CH2:23]O)[CH2:21][OH:22])=[CH:18]\[CH3:19].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH:17](/[C@@H:20]1[CH2:21][O:22][C@@H:15]([C@H:12]2[CH2:11][CH2:10][C@H:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=3)[CH2:14][CH2:13]2)[O:16][CH2:23]1)=[CH:18]\[CH3:19]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 190192522-(1E-propenyl)-1,3-propanediolHCID 178520926HCID 178520926, compound

Product 1

HCID 178448155HCID 178448155, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3.0 g of trans-4-(3,4-difluorophenyl)cyclohexanecarboxaldehyde (prepared in accordance with Example 2) and 2.4 g of 2-(1E-propenyl)-1,3-propanediol in 75 ml of toluene was treated with 3 drops of 10 percent (v/v) sulphuric acid and the reaction mixture was heated to boiling for 1.25 hours, whereby moist toluene was distilled off and replaced by fresh toluene. Then, the reaction mixture was neutralized with triethylamine and, after cooling, washed three times with water, dried over sodium sulphate and concentrated. Chromatographic purification of the residue on 100 g of silica gel with hexane/ethyl acetate (vol. 49:1) and repeated recrystallization of the trans/cis mixture from hexane gave 0.8 g of pure trans-5-(1E-propenyl)-2-[trans-4-(3,4-difluoro-phenyl)cyclohexyl]-1,3-dioxane; m.p. (C-N) 96.0° C., cl.p. (N-I) 125.5° C., Δε (115° C.)=12.4.

Workup

  1. temperaturethe reaction mixture was heated
  2. distillationwhereby moist toluene was distilled off
  3. temperatureafter cooling
  4. washwashed three times with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customChromatographic purification of the residue on 100 g of silica gel with hexane/ethyl acetate (vol. 49:1)
  8. customrecrystallization of the trans/cis mixture from hexane

Sources & evidence

ORD record
ord-3616b99d5c19480eba18bf89782b76b5
Source dataset
uspto-grants-1994_06
Patent number
US05322638

Reaction notes

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