Water → 4-(4-Butylphenylethynyl)benzoic acid

HRID 551925Notes

Reaction equation

HRID 551925 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[Li+].[OH-].O>CO>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57554541Methyl 4-[(4-butylphenyl)ethynyl]benzoate

Product 1

HCID 219465344-(4-Butylphenylethynyl)benzoic acidYield 89.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-[(4-butylphenyl)ethynyl]benzoate (23.0 g, 0.078 mol) in MeOH (200 ml) was added LiOH (3.6 g, 0.157 mol) followed by water (50 mL) and the reaction mixture was stirred for 5 hrs at rt. The solvents were removed under reduced pressure. The residue was acidified with an aqueous solution of HCl (1.5M) and a solid precipitated out. The precipitate was filtered and dried to yield 19.5 g (89%) of the title compound. 1H NMR (DMSO-d6) δ: 13.1 (brs, 1H), 7.96 (dd, J=1.6 and 6.7 Hz, 2H), 7.64 (d, J=6.8 Hz, 2H), 7.49 (d, J=8.1 Hz, 2H), 7.25 (d, J=8.2 Hz, 2H), 2.60 (t, J=7.5 Hz, 2H), 1.55 (m, 2H), 1.29 (m, 2H), 0.88 (t, J=7.3 Hz, 3H).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customa solid precipitated out
  3. filtrationThe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-71ff14b216b4443b8e3cf3c8c8e93434
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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