Hydrochloric Acid → 4-[(1-{4-[(4-Butylphenyl)ethynyl]phenyl}pentyl)oxy]-2-hydroxybenzoic acid

HRID 551914Notes

Reaction equation

HRID 551914 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([O:24][C:25]3[CH:26]=[CH:27][C:28]4[C:33](=[O:34])[O:32]C(C)(C)[O:30][C:29]=4[CH:37]=3)[CH2:20][CH2:21][CH2:22][CH3:23])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CCO>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([O:24][C:25]3[CH:26]=[CH:27][C:28]([C:33]([OH:34])=[O:32])=[C:29]([OH:30])[CH:37]=3)[CH2:20][CH2:21][CH2:22][CH3:23])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 575545257-[(1-{4-[(4-butylphenyl)ethynyl]phenyl}pentyl)oxy]-2,2-dimethyl-4H-1,3-benzodioxin-4-one

Product 1

HCID 115615764-[(1-{4-[(4-Butylphenyl)ethynyl]phenyl}pentyl)oxy]-2-hydroxybenzoic acidYield 94.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-[(1-{4-[(4-butylphenyl)ethynyl]phenyl}pentyl)oxy]-2,2-dimethyl-4H-1,3-benzodioxin-4-one (370 mg, 0.74 mmol) in EtOH (10 mL) was added an aqueous solution of NaOH (0.75 mL, 3.75 mmol, 5N) and the resulting mixture was stirred overnight at rt. An aqueous solution of HCl (10 mL, 1N) was added and the resulting reaction mixture was extracted with Et2O (3×). The combined organic layers were washed with water and brine, dried over MgSO4 and the solvents were removed under reduced pressure to give 320 mg (94%) of the title compound as a colorless oil. HPLC, Rt: 6.8 min (purity: 99.8%). LC/MS, M−(ESI): 455.3. 1H NMR (CDCl3) δ:10.5 (s, 1H); 9.66 (brs, 1H), 7.72 (d, J=9.0 Hz, 1H), 7.48 (d, J=8.3 Hz, 2H), 7.41 (d, J=8.3 Hz, 2H), 7.28 (d, J=8.3 Hz, 2H), 7.15 (d, J=8.3 Hz, 2H), 6.45 (dd, J=2.3 Hz, J=9.0 Hz, 1H), 6.35 (d, J=2.3 Hz, 1H), 5.14 (t, J=7.8 Hz, 1H), 2.61 (t, J=7.9 Hz, 2H), 2.09-1.93 (m, 1H), 1.90-1.75 (m, 1H), 1.66-1.75 (m, 1H), 1.66-1.19 (m, 8H), 0.96-0.84 (m, 6H).

Workup

  1. customthe resulting reaction mixture
  2. extractionwas extracted with Et2O (3×)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over MgSO4
  5. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-2463dc25b5c84795bd0b6c699a532826
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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