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

HRID 78871

반응식

HRID 78871 반응식
[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]

참가 물질

5

반응물 2

HCID 24386Thionyl ChlorideHCID 5398693,5-Diacetoxybenzoic Acid

생성물 1

HCID 11368883(3-Acetyloxy-5-carbonochloridoylphenyl) acetate수율 95.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-93b2374d6a4e451ea4840403a5f394bb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841477B2

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