Hydrochloric Acid → HCID 53963884, compound

HRID 613169Notes

Reaction equation

HRID 613169 reaction equation
[CH3:1][Si:2]([CH3:17])([CH3:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1)C(O)=O.[C:18](=[O:21])([O-:20])[O-].[K+].[K+].S(Cl)(Cl)=O.CN(C)C=O.C(N(CC)CC)C.[CH3:40][O:41][C:42]([C:44]1[CH:45]=[CH:46][C:47](O)=[CH:48][CH:49]=1)=[O:43].Cl>C1C=CC=CC=1>[CH3:17][Si:2]([CH3:1])([CH3:16])[C:3]1[CH:4]=[C:5]([O:20][C:18]([C:47]2[CH:46]=[CH:45][C:44]([C:42]([O:41][CH3:40])=[O:43])=[CH:49][CH:48]=2)=[O:21])[CH:9]=[C:10]([Si:12]([CH3:13])([CH3:14])[CH3:15])[CH:11]=1

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 7456MethylparabenHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 146056473,5-Bis(trimethylsilyl)benzoic acid

Product 1

HCID 53963884HCID 53963884, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 665 mg (2.5 mmol) of 3,5-bis(trimethylsilyl)benzoic acid and 670 mg of potassium carbonate in dry benzene were added 0.40 ml (5.5 mmol) of thionyl chloride and 0.21 ml (2.75 mmol) of N,N-dimethylformamide at room temperature with stirring. The mixture was stirred at room temperature for 3 hours. The insoluble matter was filtered off and the filtrate was evaporated. The residue was dissolved in 17.5 ml of dry tetrahydrofuran and 0.77 ml (5.5 mmol) of triethylamine and 418 mg (2.75 mmol) of methyl p-hydroxybenzoate were added to the solution. The mixture was stirred at room temperature for 1 day. The reaction mixture was made weakly acid with hydrochloric acid and extracted with methylene chloride. The extract was successively washed with water and sat.aq.NaCl, dried over anhyd.Na2SO4 and evaporated.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. filtrationThe insoluble matter was filtered off
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in 17.5 ml of dry tetrahydrofuran
  5. stirringThe mixture was stirred at room temperature for 1 day
  6. extractionextracted with methylene chloride
  7. washThe extract was successively washed with water and sat.aq
  8. dry with materialNaCl, dried over anhyd
  9. customNa2SO4 and evaporated

Sources & evidence

ORD record
ord-7fd23091f7874ec1877c07dac77d73d7
Source dataset
uspto-grants-1999_12
Patent number
USRE036477

Reaction notes

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