3-Fluorobenzaldehyde → 5-Propyl-2-(3-fluorophenyl)-1,3-dioxane

HRID 342327Notes

Reaction equation

HRID 342327 reaction equation
[CH2:1]([CH:4]([CH2:7][OH:8])[CH2:5][OH:6])[CH2:2][CH3:3].[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O>C1(C)C=CC=CC=1>[CH2:1]([CH:4]1[CH2:7][O:8][CH:13]([C:12]2[CH:15]=[CH:16][CH:17]=[C:10]([F:9])[CH:11]=2)[O:6][CH2:5]1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 680093-FluorobenzaldehydeHCID 70211562-propylpropane-1,3-diol

Product 1

HCID 542446685-Propyl-2-(3-fluorophenyl)-1,3-dioxaneYield 32.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Propyl-1,3-propanediol (138.0 g; 1.17 mol) and 3-fluorobenzaldehyde (138.0 g; 1.11 mol) were dissolved in toluene (1.5 liters), and PTS (7 g) was added. The mixture was refluxed for 3 hours while being dehydrated with a Dean-Stark's device. The resultant reaction mixture was washed sequentially with saturated sodium bicarbonate solution and saturated brine, and then dried over magnesium sulfate. Subsequently, the solvent was evaporated. The residue was recrystallized twice from heptane, to thereby obtain 81.2 g (362 mmol) of 5-propyl-2-(3-fluorophenyl)-1,3-dioxane. The yield of the compound from 3-fluorobenzaldehyde was 32.6%.

Workup

  1. additionPTS (7 g) was added
  2. temperatureThe mixture was refluxed for 3 hours
  3. customThe resultant reaction mixture
  4. washwas washed sequentially with saturated sodium bicarbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customSubsequently, the solvent was evaporated
  7. customThe residue was recrystallized twice from heptane

Sources & evidence

ORD record
ord-58ffe98ff8d0438ca2f921319ac60a83
Source dataset
uspto-grants-1999_01
Patent number
US05858272

Reaction notes

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