m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

HRID 389357ノート

反応式

HRID 389357 の反応式
[C:1]([O:6][CH:7]([O:9][C:10]([O:12][CH:13]1[CH2:18][C:17](=[O:19])[NH:16][C:14]1=[O:15])=[O:11])[CH3:8])(=[O:5])[CH:2]([CH3:4])[CH3:3].ON1C(=O)CCC1=O.C(=O)(SC(C)(C)C)OC(OC(=O)C(C)C)C.[Cl:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([O:53]O)=[O:52])[CH:46]=1>C(Cl)Cl.CCOCC>[C:1]([O:6][CH:7]([O:9][C:10]([O:12][CH:13]1[CH2:18][C:17](=[O:19])[NH:16][C:14]1=[O:15])=[O:11])[CH3:8])(=[O:5])[CH:2]([CH3:4])[CH3:3].[Cl:44][C:45]1[CH:46]=[C:47]([CH:48]=[CH:49][CH:50]=1)[C:51]([OH:53])=[O:52]

参加物

8

反応物 4

HCID 70297m-Chloroperbenzoic acidHCID 80170N-HydroxysuccinimideHCID 66743414[(1-Isobutanoyloxyethoxy)carbonyloxy]succinimideHCID 86615734O-(1-Isobutanoyloxyethyl) S-tert-Butyl Thiocarbonate

生成物 2

HCID 4473-Chlorobenzoic AcidHCID 66743414[(1-Isobutanoyloxyethoxy)carbonyloxy]succinimide

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

In still another alternative synthesis of (10), N-hydroxysuccinimide (230 mg, 2 mmol) was added to a solution of compound (8) (248 mg, 1 mmol) in CH2Cl2 (10 mL) was added and the reaction mixture cooled to 0° C. m-Chloroperbenzoic acid (670 mg, 3 mmol, commercial grade: 77% in water) was added over a period of 10 min and the mixture allowed to stir at room temperature for 16 h. The reaction mixture was diluted with ether (50 mL) and washed with water (2×10 mL), saturated sodium bicarbonate solution (10 mL) and brine (10 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound (10) together with m-chlorobenzoic acid. The crude product mixture was purified by column chromatography on silica gel, eluting with 4:6 EtOAc:hexane. Residual m-chlorobenzoic acid was removed by repeated crystallizations from a mixture of tert-butyl methyl ether and hexane which resulted in analytically pure product (30 mg, 11%).

後処理

  1. additionwas added
  2. additionwas added over a period of 10 min
  3. washwashed with water (2×10 mL), saturated sodium bicarbonate solution (10 mL) and brine (10 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e3e2fb32e1734e58aba26afd5e62ae0f
出典データセット
uspto-grants-2013_02
特許番号
US08378137B2

反応ノート

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