Hydrochloric Acid → HCID 54014406, compound

HRID 466327Notes

Reaction equation

HRID 466327 reaction equation
[OH-].[K+].[CH3:3][Si:4]([CH3:24])([CH3:23])[C:5]1[CH:6]=[C:7](/[CH:11]=[CH:12]/[C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)[CH:8]=[CH:9][CH:10]=1.Cl>CCO>[CH3:24][Si:4]([CH3:3])([CH3:23])[C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:21][CH:22]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14605658trans-Methyl 4-[(3-trimethylsilylphenyl)ethenyl]benzoate

Product 1

HCID 54014406HCID 54014406, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.8 ml (3.6 mmol) of 2N-KOH was added to a solution of 143 mg (0.461 mmol) of trans-methyl 4-[(3-trimethylsilylphenyl)ethenyl]benzoate in 3 ml of EtOH. The mixture was stirred at room temperature. The reaction mixture was adjusted to acid pH with 2N hydrochloric acid, and then the aqueous solution was extracted with AcOEt. The extract was dried and evaporated to give 137 mg of the title compound as white crystals (yield 100%), which were recrystallized from a mixture of ethyl acetate, methylene chloride and n-hexane, and dried to give 116 mg of white crystals, m.p. 216°-218° C. (yield 85%).

Workup

  1. extractionthe aqueous solution was extracted with AcOEt
  2. customThe extract was dried
  3. customevaporated

Sources & evidence

ORD record
ord-2f485639bf364f6ba645cba22fa4e1ac
Source dataset
uspto-grants-1992_10
Patent number
US05155249

Reaction notes

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