Lithium Hydroxide → 2-Chloro-5-{[(3-chlorophenyl)methyl]oxy}benzoic acid

HRID 1879104

Reaction equation

HRID 1879104 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)=[CH:15][C:3]=1[C:4]([O:6]CC1C=CC=C(Cl)C=1)=[O:5].[OH-].[Li+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)=[CH:15][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59760043(3-Chlorophenyl)methyl 2-chloro-5-{[(3-chlorophenyl)methyl]oxy}benzoate

Product 1

HCID 597600492-Chloro-5-{[(3-chlorophenyl)methyl]oxy}benzoic acidYield 87.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (3-chlorophenyl)methyl 2-chloro-5-{[(3-chlorophenyl)methyl]oxy}benzoate (970 mg, 2.3 mmol) in dioxane (30 ml) and water (15 ml) was treated with lithium hydroxide (monohydrate) (145 mg, 3.5 mmol, 1.5 eq). The resulting mixture was stirred at room temperature for 2 hours. The solvent was then evaporated in vacuo, the residue take up into water (50 ml) and washed with ether (100 ml). The aqueous layer was then acidified with 2M HCl the extracted with ether (2×150 ml). Organic layers combined, washed with brine, dried and evaporated in vacuo to afford the title product as a white solid (600 mg). MS (ES−) m/z 295 [M−H]− (C14H1035Cl2O3). 1H-NMR (400 MHz, d6-DMSO) δ 5.17 (2H, s), 7.17-7.20 (1H, m), 7.38-7.53 (6H, m), 13.4 (1H, s).

Workup

  1. customThe solvent was then evaporated in vacuo
  2. washwashed with ether (100 ml)
  3. extractionextracted with ether (2×150 ml)
  4. washwashed with brine
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-c62acdd9fd5c45ae8bab147d1613d69c
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Linked notes

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