Hydrochloric Acid → 4-[1-Hydroxy-3-(2-hydroxy-5-trimethylsilylphenyl)-3-oxo-1-propenyl]benzoic Acid

HRID 466338Notes

Reaction equation

HRID 466338 reaction equation
[OH:1][C:2]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=1)=[CH:3][C:4]([C:6]1[CH:11]=[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:9]=[CH:8][C:7]=1[OH:16])=[O:5].[OH-].[Na+].Cl>C(O)C>[OH:1][C:2]([C:17]1[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=1)=[CH:3][C:4]([C:6]1[CH:11]=[C:10]([Si:12]([CH3:15])([CH3:13])[CH3:14])[CH:9]=[CH:8][C:7]=1[OH:16])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67558861HCID 67558861, compound

Product 1

HCID 675585414-[1-Hydroxy-3-(2-hydroxy-5-trimethylsilylphenyl)-3-oxo-1-propenyl]benzoic AcidYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 148 mg (0.4 mmol) of methyl 4-[1-hydroxy-3(2-hydroxy-5-trimethylsilylphenyl)-3-oxo-1-propenyl]benzoate in 20 ml of ethanol was added 2 ml of 2N-sodium hydroxide solution at room temperature with stirring. The mixture was stirred at room temperature for 1 day and acidified with 10%-hydrochloric acid to pH 4. A deposited precipitation was extracted with AcOEt. The extract was washed with H2O and saturated aq.NaCl, dried over MgSO4, and evaporated. The residue was recrystallized from methanol to give 72 mg of yellow needles (yield 51%), m.p. 207°-209° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 day
  2. customA deposited precipitation
  3. extractionwas extracted with AcOEt
  4. washThe extract was washed with H2O
  5. dry with materialNaCl, dried over MgSO4
  6. customevaporated
  7. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-f891492f467040219dc2d6fd6f598acb
Source dataset
uspto-grants-1992_10
Patent number
US05155249

Reaction notes

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