2,2-Dimethoxypropane → HCID 67356722, compound

HRID 577827Notes

Reaction equation

HRID 577827 reaction equation
[F:1][C:2]1[C:9]([F:10])=[C:8]([F:11])C=C[C:3]=1[CH:4]=O.[CH3:12][O:13][C:14]([O:17][CH3:18])(C)[CH3:15]>CCOCC.CC1C=CC(S(O)(=O)=O)=CC=1>[CH3:12][O:13][CH:14]([O:17][CH3:18])[C:15]1[CH:4]=[CH:3][C:2]([F:1])=[C:9]([F:10])[C:8]=1[F:11]

Participants

5

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 5192262,3,4-Trifluorobenzaldehyde

Product 1

HCID 67356722HCID 67356722, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2,3,4-trifluorobenzaldehyde (25 g, 156.16 mmol), 2,2-dimethoxypropane (58.1 ml, 468.48 mmol), and 4-methylbenzenesulfonic acid (0.269 g, 1.56 mmol) was stirred at room temperature overnight. The reaction mixture diluted with ether and washed successively with aq. sodium bicarbonate solution, water, and brine. The organic layer dried over sodium sulfate and concentrated. The residue was distilled under high vacuum to give the title compound (23.07 g, 71.7%).

Workup

  1. washwashed successively with aq. sodium bicarbonate solution, water, and brine
  2. dry with materialThe organic layer dried over sodium sulfate
  3. concentrationconcentrated
  4. distillationThe residue was distilled under high vacuum

Sources & evidence

ORD record
ord-73668a9afa6d497f8d3d0788b8be06b6
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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