p-Toluenesulfonic acid → HCID 57437442, compound

HRID 1665972Notes

Reaction equation

HRID 1665972 reaction equation
[Br:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:11].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:23](O)[CH2:24][CH2:25][OH:26]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([CH:6]2[O:26][CH2:25][CH2:24][CH2:23][O:7]2)=[CH:8][C:9]=1[CH3:10]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 222596864-Bromo-3,5-dimethylbenzaldehyde

Product 1

HCID 57437442HCID 57437442, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-bromo-3,5-dimethyl-benzaldehyde (8.15 g, 38.25 mmol), p-toluenesulfonic acid (50 mg) and 1,3-propanediol (9.5 mL) in toluene (100 mL) is heated to 110° C. for 3 h. The reaction flask is equipped with a Dean-Stark apparatus and heating is continued at 110° C. for 16 h. The reaction mixture is cooled to rt, washed with sat. aq. NaHCO3 and the solvent is removed in vacuo. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 2-(4-bromo-3,5-dimethyl-phenyl)-[1,3]dioxane (5.97 g) as a colourless oil.

Workup

  1. customThe reaction flask is equipped with a Dean-Stark apparatus
  2. temperatureheating
  3. washwashed with sat. aq. NaHCO3
  4. customthe solvent is removed in vacuo
  5. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

Sources & evidence

ORD record
ord-0b4c5ef06d414ddf9cc5f4d80a8bf544
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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