p-Toluenesulfonic acid → HCID 67416155, compound

HRID 2261433Notes

Reaction equation

HRID 2261433 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([OH:12])[CH2:10][OH:11])=[CH:4][CH:3]=1.[C:13]1(C)[CH:18]=CC(S(O)(=O)=O)=C[CH:14]=1>CN(C=O)C.COC(OC)(C)C.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]2[CH2:10][O:11][C:13]([CH3:18])([CH3:14])[O:12]2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 203327403-(4-Bromophenyl)propane-1,2-diol

Product 1

HCID 67416155HCID 67416155, compoundYield 1,994.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 64952,2-DimethoxypropaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 3-(4-bromo-phenyl)-propane-1,2-diol (1.41 g, 6.10 mmol) and p-toluenesulfonic acid (50 mg) in DMF (10 mL), 2,2-dimethoxypropane (10 mL) is stirred at rt for 2 h. The reaction mixture is diluted with sat. aq. NaHCO3 (150 mL) and extracted with diethyl ether (2×200 mL). The organic extracts are washed with water (200 mL), dried over MgSO4 and evaporated to give 4-(4-bromo-benzyl)-2,2-dimethyl-[1,3]dioxolane (1.57 g) as a pale brownish oil; LC-MS: tR=1.00 min.

Workup

  1. extractionextracted with diethyl ether (2×200 mL)
  2. washThe organic extracts are washed with water (200 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-3dad60c7be5542839601bd05ca49732a
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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