Thionyl Chloride → (3-Acetyloxy-5-carbonochloridoylphenyl) acetate

HRID 78871

反応式

HRID 78871 の反応式
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:14][C:15](=[O:17])[CH3:16])[CH:13]=1)[C:8](O)=[O:9])(=[O:3])[CH3:2].S(Cl)([Cl:20])=O>CN(C)C=O.C1(C)C=CC=CC=1>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:14][C:15](=[O:17])[CH3:16])[CH:13]=1)[C:8]([Cl:20])=[O:9])(=[O:3])[CH3:2]

参加物

5

反応物 2

HCID 24386Thionyl ChlorideHCID 5398693,5-Diacetoxybenzoic Acid

生成物 1

HCID 11368883(3-Acetyloxy-5-carbonochloridoylphenyl) acetate収率 95.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 1140Toluene溶媒

実験手順

To a mixture of 3,5-diacetoxybenzoic acid (8.00 g, 33.59 mmol) and dimethylformamide (5 drops) in toluene was added freshly distilled thionylchloride (16 mL). The mixture was stirred for 15 min under nitrogen atmosphere at ambient temperature. Then it was refluxed for 2 h at 80° C. in a hot water bath. The excess thionyl chloride was evaporated in vacuo and toluene was added. Insoluble yellow solid was discarded. Toluene was evaporated in vacuo and gave 3,5-diacetoxybenzoyl chloride (8.23 g, 95.5%), which can be recrystallized from hexane. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.75 (d, 2H), 7.29 (t, 1H), 2.34 (s, 6H); 13C NMR (CDCl3, 75 MHz) δ 168.8, 167.0, 151.4, 135.3, 122.8, 122.0, 21.2; mp=89.5-91° C.; HRMS (EI+) found 256.0130 M+, calcd 256.0139 for C11H9O5Cl; Anal. Calcd for C11H9O5Cl: C, 51.48; H, 3.53. Found: C, 51.60; H, 3.68.

後処理

  1. temperatureThen it was refluxed for 2 h at 80° C. in a hot water bath
  2. customThe excess thionyl chloride was evaporated in vacuo and toluene
  3. additionwas added
  4. customToluene was evaporated in vacuo

出典と根拠

ORDレコード
ord-93b2374d6a4e451ea4840403a5f394bb
出典データセット
uspto-grants-2014_09
特許番号
US08841477B2

関連ノート

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