2,2-Dimethoxypropane → HCID 67356722, compound

HRID 245373Notes

Reaction equation

HRID 245373 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 wasdistilled 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

Sources & evidence

ORD record
ord-ac8141f9b0d146089b64d53c6e1b46c8
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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