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

HRID 1879104

반응식

HRID 1879104 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c62acdd9fd5c45ae8bab147d1613d69c
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314147B2

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