Potassium Hydroxide → 3-[4-(5-tert-Butyl-2-methyl-phenylethynyl)-phenyl]-acrylic acid

HRID 2377433Notes

Reaction equation

HRID 2377433 reaction equation
C([O:3][C:4](=[O:26])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=[CH:17][C:16]=2[CH3:25])=[CH:9][CH:8]=1)C.[OH-].[K+]>C(O)C.O1CCCC1>[C:21]([C:19]1[CH:18]=[CH:17][C:16]([CH3:25])=[C:15]([C:14]#[C:13][C:10]2[CH:11]=[CH:12][C:7]([CH:6]=[CH:5][C:4]([OH:26])=[O:3])=[CH:8][CH:9]=2)[CH:20]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 690739133-[4-(5-tert-Butyl-2-methyl-phenylethynyl)-phenyl]-acrylic acid ethyl ester2×

Product 1

HCID 690781133-[4-(5-tert-Butyl-2-methyl-phenylethynyl)-phenyl]-acrylic acidYield 77.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[4-(5-tert-butyl-2-methyl-phenylethynyl)-phenyl]-acrylic acid ethyl ester (Intermediate 111, 0.09 g, 0.26 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with 3M potassium hydroxide solution (1 mL, 3 mmol) and the resulting reaction mixture was stirred overnight at ambient temperature. The reaction mixture was concentrated in vacuo slightly, the residue was neutralized with dilute hydrochloric acid, and the solid that was formed was filtered and washed with water and acetonitrile and dried to afford title product (0.064 g, 77%).

Workup

  1. customthe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo slightly
  3. customthe solid that was formed
  4. filtrationwas filtered
  5. washwashed with water and acetonitrile
  6. customdried

Sources & evidence

ORD record
ord-fb49e75273e54b878aaabf117763737c
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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