Chlorotrimethylsilane → HCID 53962653, compound

HRID 1915505Notes

Reaction equation

HRID 1915505 reaction equation
C[Si](Cl)(C)C.C(=O)([O:12][C:13]1[C:18]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=1[C:23]([CH3:26])([CH3:25])[CH3:24])OC(C)(C)C.[N+:28]([O-])([O-:30])=[O:29].[K+].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)(Cl)Cl>[C:23]([C:14]1[C:15]([N+:28]([O-:30])=[O:29])=[CH:16][CH:17]=[C:18]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]=1[OH:12])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 24434Potassium NitrateHCID 5169563HCID 5169563, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 53962653HCID 53962653, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

TMSCl (8.5 g, 78.24 mmol) and tert-butyl (2,6-di-tert-butylphenyl) carbonate (12.0 g, 39.16 mmol) was added to a suspension of KNO3 (5.9 g, 58.36 mmol) in CHCl3 (100 mL) successively at 0° C. The reaction mixture was stirred for 0.5 h and AlCl3 (15.5 g, 116.20 mmol) was added. The stirring was continued for 2 h and the resulting mixture was poured into ice-water and extracted with CH2Cl2. The combined organic layers were washed with sat. NaHCO3 solution and brine, dried over Na2SO4 and evaporated in vacuo. The crude product was purified by silica gel column chromatography (petroleum ether) to give 2,6-di-tert-butyl-3-nitrophenol (2.5 g, 25%). 1H NMR (300 MHz, CDCl3) δ 7.18 (d, J=8.4 Hz, 1H), 6.79 (d, J=8.4 Hz, 1H), 5.57 (s, 1H), 1.51 (s, 9H), 1.44 (s, 9H).

Workup

  1. waitThe stirring was continued for 2 h
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layers were washed with sat. NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo
  6. customThe crude product was purified by silica gel column chromatography (petroleum ether)

Sources & evidence

ORD record
ord-453b6f2263b34a9caa5b379a5c63b29e
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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