Water → 4-(1,3-Dioxan-2-yl)-3-fluorobenzonitrile

HRID 336899Notes

Reaction equation

HRID 336899 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([F:11])[CH:4]=1)#[N:2].[CH2:12](O)[CH2:13][CH2:14][OH:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[O:8]1[CH2:12][CH2:13][CH2:14][O:15][CH:7]1[C:6]1[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[F:11]

Participants

6

Reactant 4

HCID 962WaterHCID 104421,3-PropanediolHCID 521998p-Toluenesulfonic acid monohydrateHCID 27831503-Fluoro-4-formylbenzonitrile

Product 1

HCID 580325814-(1,3-Dioxan-2-yl)-3-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Cyano-2-fluorobenzaldehyde (65 g, 436 mmol) and 1,3-propanediol (36.5 g, 479 mmol; 1.1 eq.) were, together with 4-toluenesulfonic acid monohydrate (1.66 g, 8.72 mmol; 0.02 eq.), initially charged in toluene (1000 ml) and stirred at boiling point on a water separator for 6 h. The reaction mixture was then washed with saturated sodium bicarbonate solution (3×300 ml) and saturated sodium chloride solution (3×300 ml). The organic phase was dried over sodium sulfate and concentrated. The title compound was obtained as a solid (92 g, quant.).

Workup

  1. washThe reaction mixture was then washed with saturated sodium bicarbonate solution (3×300 ml) and saturated sodium chloride solution (3×300 ml)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cf324b088c48437681fd7541887522e5
Source dataset
uspto-grants-2014_11
Patent number
US08889700B2

Reaction notes

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