p-Toluenesulfonic acid → 5-Pentyl-2-(3',4'-difluorophenyl)-1,3-dioxane

HRID 1494662Notes

Reaction equation

HRID 1494662 reaction equation
[CH2:1]([CH:6]([CH2:9][OH:10])[CH2:7][OH:8])[CH2:2][CH2:3][CH2:4][CH3:5].[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[F:20])[CH:15]=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.C(Cl)(Cl)Cl.C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:1]([CH:6]1[CH2:9][O:10][CH:15]([C:14]2[CH:17]=[CH:18][C:19]([F:20])=[C:12]([F:11])[CH:13]=2)[O:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

8

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 1175092-Pentyl-1,3-propanediolHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 157450915-Pentyl-2-(3',4'-difluorophenyl)-1,3-dioxane

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Four solutions were prepared by dissolving 11.8 g (0.10 mol) of 2-pentylpropane-1,3-diol (prepared in Example 1 following the procedures of Steps 1-2), 14.2 g (0.10 mol) of 3,4-difluorobenzaldehyde, and 0.9 g (0.005 mol) of p-toluenesulfonic acid in methylene chloride (b.p. 40° C.), chloroform (b.p. 60° C.), benzene (b.p. 80° C.) and toluene (b.p. 111° C.), respectively. The solutions were treated following the procedures of Step 3 of Example 1 to yield mixtures of the cis and trans isomers of 5-pentyl-2-(3',4'-difluorophenyl)-1,3-dioxane. The yields of each mixture from its respective solvent and the ratio of the trans isomer to the cis isomer of each mixture are shown in Table 1.

Workup

  1. customFour solutions were prepared
  2. additionThe solutions were treated

Sources & evidence

ORD record
ord-190626fadd6846cc878bb5c493d1c370
Source dataset
uspto-grants-1991_06
Patent number
US05026879

Reaction notes

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