p-Toluenesulfonic acid → 1-(4'-Pentyl-2-fluorobiphenyl-4-yl)-2-(5-heptyl-1,3-dioxan-2-yl)-ethane

HRID 246871

Reaction equation

HRID 246871 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH:20]=[O:21])=[CH:14][C:13]=2[F:22])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C1OC1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:37]([CH:44]([CH2:47]O)[CH2:45][OH:46])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH:20]3[O:46][CH2:45][CH:44]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:47][O:21]3)=[CH:14][C:13]=2[F:22])=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

8

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 6354Ethylene OxideHCID 2255562-Heptylpropane-1,3-diolHCID 201626933-(4'-Pentyl-2-fluorobiphenyl-4-yl)-propionaldehydeHCID 178418287HCID 178418287, compound

Product 1

HCID 201625331-(4'-Pentyl-2-fluorobiphenyl-4-yl)-2-(5-heptyl-1,3-dioxan-2-yl)-ethane

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

6 g of 3-(4'-pentyl-2-fluorobiphenyl-4-yl)-propionaldehyde (obtainable by reaction of 4-(2-fluoro-4'-pentylbiphenylyl)-magnesium bromide with ethylene oxide and subsequent oxidation of the resulting alcohol with pyridinium chlorochromate) and 3.5 g of 2-heptylpropane-1,3-diol are heated with a spatula tip of p-toluenesulfonic acid in 100 ml of toluene, using a water separator, until no further water is foamed. After cooling, the mixture is washed with bicarbonate solution and water until neutral and dried over sodium sulfate and the toluene is distilled off. After customary working-up, 1-(4'-pentyl-2-fluorobiphenyl-4-yl)-2-(5-heptyl-1,3-dioxan-2-yl)-ethane is obtained.

Workup

  1. temperatureAfter cooling
  2. washthe mixture is washed with bicarbonate solution and water until neutral and
  3. dry with materialdried over sodium sulfate
  4. distillationthe toluene is distilled off

Sources & evidence

ORD record
ord-4b3486c85a834ce6bb8d008df64f872d
Source dataset
uspto-grants-1987_11
Patent number
US04704227

Linked notes

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