Water → 2-(4-Isobutylphenyl)acrylic acid

HRID 1588964Notes

Reaction equation

HRID 1588964 reaction equation
[F-].[K+].[CH2:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13](=[CH:17][Si](CC)(CC)CC)[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)[CH:4]([CH3:6])[CH3:5].O>C(#N)C>[CH2:3]([C:7]1[CH:8]=[CH:9][C:10]([C:13](=[CH2:17])[C:14]([OH:16])=[O:15])=[CH:11][CH:12]=1)[CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 522689Potassium Fluoride2×HCID 67882316alpha-(4'-Isobutylphenyl)-beta-triethylsilyl acrylic acid

Product 1

HCID 111273872-(4-Isobutylphenyl)acrylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

This desilylation (elimination) reaction may be performed, for example, by following the procedure of T. H. Chan et al. referred to above. A catalyst such as, for example, potassium fluoride is used for desilylation. α-(4'-isobutylphenyl)-β-triethylsilyl acrylic acid from Example 4 (0.02 mol) is dissolved in a suitable solvent such as, for example, acetonitrile (15-20 ml). Potassium fluoride (0.025 mol) is added to the solution, and the mixture stirred at a suitable temperature such as, for example, ambient temperature, for a suitable time, for example, about 2-10 hours. The contents are poured into water (about 20 ml), and transferred to a separatory funnel. The separated organic layers are washed with water, then dried (with MgSO4), and evaporated in vacuo to isolate the desilylated acrylic acid, which may be purified by conventional methods, if so desired.

Workup

  1. customThis desilylation (elimination) reaction
  2. customfor example, about 2-10 hours
  3. customtransferred to a separatory funnel
  4. washThe separated organic layers are washed with water
  5. dry with materialdried (with MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-a8c8102d6c99400c96454ec47146aa84
Source dataset
uspto-grants-1993_06
Patent number
US05223640

Reaction notes

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