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

HRID 1879104

反応式

HRID 1879104 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c62acdd9fd5c45ae8bab147d1613d69c
出典データセット
uspto-grants-2012_11
特許番号
US08314147B2

関連ノート

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