p-Toluenesulfonic acid → 4-Allyldimethylsilylbenzaldehyde

HRID 2228378Notes

Reaction equation

HRID 2228378 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2OCC[O:11]2)=[C:6]([SiH:15]([CH3:17])[CH3:16])[CH:5]=1)[CH:2]=[CH2:3].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[C:6]([SiH:15]([CH3:17])[CH3:16])[CH:5]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 1317233722-(4-Allyldimethylsilylphenyl)1,3-dioxolane

Product 1

HCID 1317233714-AllyldimethylsilylbenzaldehydeYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-(4-allyldimethylsilylphenyl)-1,3-dioxolane (3 Scheme 18, 12 g, 52.5 mmol) and p-toluenesulfonic acid (100 mg) in acetone (300 mL) was heated under reflux for 3 h. The reaction mixture was concentrated under reduced pressure, and acetone (300 mL) was added to the residue. After refluxing for 3 h, the solution was concentrated, and the crude oil was purified by silica gel chromatography (1:20 ethyl acetate/hexanes) to afford a colorless oil (9.2 g, 86%); 1H NMR (300 MHz, CDCl3) δ 0.32 (s, 6 H), 1.78 (d, J=8.10 Hz, 2 H), 4.84 (s, 1 H) 4.89 (m, 1 H), 5.76 (m, 1 H), 7.67 (d, J=8.10 Hz, 2 H), 7.85 (d, J=8.10 Hz, 2 H), 10.05 (s, 1 H); 13C NMR (75 MHz, CDCl3) −3.4 (2C), 23.5, 114.2, 128.8 (2C) 133.7, 134.4, (2C), 136.9, 147.6, 192.8; HRMS calcd for C12H16OSi 204.0971, found 204.0972.

Workup

  1. temperatureunder reflux for 3 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and acetone (300 mL)
  3. additionwas added to the residue
  4. temperatureAfter refluxing for 3 h
  5. concentrationthe solution was concentrated
  6. customthe crude oil was purified by silica gel chromatography (1:20 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-356900b20d3a4591a8516e8181b7a59e
Source dataset
uspto-grants-2002_07
Patent number
US06416861B1

Reaction notes

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