Toluene → HCID 178506026, compound

HRID 2396658Notes

Reaction equation

HRID 2396658 reaction equation
[F:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:8][OH:9])[CH2:6][OH:7].[F:10][C:11]1[CH:12]=[C:13]([C:18]2[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=2)[CH:14]=[CH:15][C:16]=1[F:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[F:10][C:11]1[CH:12]=[C:13]([C:18]2[CH:25]=[CH:24][C:21]([C@H:22]3[O:9][CH2:8][C@H:5]([CH2:4][CH2:3][CH2:2][F:1])[CH2:6][O:7]3)=[CH:20][CH:19]=2)[CH:14]=[CH:15][C:16]=1[F:17]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 149852082-(3-Fluoropropyl)propane-1,3-diolHCID 151808503',4'-Difluoro[1,1'-biphenyl]-4-carbaldehyde

Product 1

HCID 178506026HCID 178506026, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.1 m of 2-(3-fluoropropyl)-1,3-propanediol, 0.1 m of p-(3,4-difluorophenyl)benzaldehyde (prepared by cross-coupling as described above), 1 g of p-toluenesulfonic acid and 200 ml of toluene is boiled for 1 hour on a water separator. Extractive work-up and purification by crystallization and chromatography give trans-2-(3,4-difluorobiphenyl-4'-yl)-5-(3-fluoropropyl)-1,3-dioxane.

Workup

  1. customExtractive work-up and purification
  2. customby crystallization and chromatography

Sources & evidence

ORD record
ord-470f5a908ba441678ea0e0923580f26f
Source dataset
uspto-grants-1996_02
Patent number
US05494606

Reaction notes

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