Triethylsilane → 4-(2,3,4,5-tetramethoxy-6-methylbenzyl)benzoic Acid

HRID 496348Notes

Reaction equation

HRID 496348 reaction equation
C([SiH](CC)CC)C.O[CH:9]([C:19]1[C:24]([CH3:25])=[C:23]([O:26][CH3:27])[C:22]([O:28][CH3:29])=[C:21]([O:30][CH3:31])[C:20]=1[O:32][CH3:33])[C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1>C(Cl)Cl.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C>[CH3:33][O:32][C:20]1[C:21]([O:30][CH3:31])=[C:22]([O:28][CH3:29])[C:23]([O:26][CH3:27])=[C:24]([CH3:25])[C:19]=1[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 22325281HCID 22325281, compound

Product 1

HCID 223252774-(2,3,4,5-tetramethoxy-6-methylbenzyl)benzoic AcidYield 96%

Reagents, catalysts & solvents 2

HCID 65367Trimethylsilyl triflateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of triethylsilane (1.39 ml, 8.74 mmol) and TMSOTf (0.056 ml, 0.31 mmol) in methylene chloride (30 ml) was added dropwise a solution of the compound (2.26 g, 6.24 mmol) obtained in Step 1 in methylene chloride (12 ml) and the mixture was stirred at room temperature for 4 hours. The reaction mixture was washed with water, dried, and then the solvent was distilled off to yield the title compound (1.98 g, 5.75 mmol, yield 96%).

Workup

  1. washThe reaction mixture was washed with water
  2. customdried
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-6dcf29f63b5f47f583cc455d350db00f
Source dataset
uspto-grants-2005_09
Patent number
US06943196B1

Reaction notes

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