Hydrochloric Acid → HCID 22238659, compound

HRID 1743277Notes

Reaction equation

HRID 1743277 reaction equation
[Mg].Br[C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:10].[CH2:11]([Si:14](OC)([O:17][CH3:18])[O:15][CH3:16])[CH2:12][CH3:13].Cl>CCOCC>[CH3:10][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([CH3:9])[C:3]=1[Si:14]([CH2:11][CH2:12][CH3:13])([O:17][CH3:18])[O:15][CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 61254TrimethoxypropylsilaneHCID 684712-Bromo-m-xyleneHCID 5462224Magnesium

Product 1

HCID 22238659HCID 22238659, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 500 mL round bottomed flask was charged with magnesium powder (2.1 g, 86 mmol, Aldrich) and ether (250 mL, Aldrich). 2-Bromo-m-xylene (9.0 mL, 68 mmol, Aldrich) was added over a 25 minute period. The contents were refluxed overnight (18 hours). The brown solution was cooled to room temperature and propyl-trimethoxysilane (17.8 mL, 101 mmol) was added over 20 minutes. A white precipitate formed. The contents were stirred at room temperature overnight (18 hours). The reaction was poured into 0.2N aqueous HCl (500 mL), the layers were separated and the product extracted into ether (3×150 mL). The combined organic portions were dried (MgSO4), filtered, and the solvent removed via rotary evaporation (13.5 g crude). Distillation under reduced pressure (b.p. 57° C., 0.04 mm Hg) provided (2,6-dimethylphenyl)-propyl-dimethoxysilane (6.8 g, 28 mmol, 41% yield); C13H22SiO2 (Mw=238.40); 1H NMR (CDCl3) δ 7.2 (t, 1H), 7.0 (d, 2H), 3.6 (s, 6H), 2.5 (s, 6H), 1.4 (m, 2H), 1.0 (t, 3H), 0.9 (t, 2H); 13C NMR (CDCl3) δ 145.2, 131.0, 129.6, 128.0, 49.8, 23.4, 17.9, 16.7, 16.3; MS m/z (relative abundance) 238 (8), 195 (100), 165 (22), 133 (12), 119 (10), 105 (13), 91 (9), 59 (16).

Workup

  1. temperatureThe contents were refluxed overnight (18 hours)
  2. customA white precipitate formed
  3. customthe layers were separated
  4. extractionthe product extracted into ether (3×150 mL)
  5. dry with materialThe combined organic portions were dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed via rotary evaporation (13.5 g crude)
  8. distillationDistillation under reduced pressure (b.p. 57° C., 0.04 mm Hg)

Sources & evidence

ORD record
ord-4dbc3b6385d043b58e73e0a0adec8cbb
Source dataset
uspto-grants-2006_03
Patent number
US07009015B2

Reaction notes

Loading…