반응 #166053

반응 방정식

3,5-diacetoxybenzoic acid

thionylchloride

→

3,5-diacetoxybenzoyl chloride

수율 95.5%

용매

toluene

반응 조건

후처리

1. 1
   온도Then it was refluxed for 2 h at 80° C. in a hot water bath
2. 2
   기타The excess thionyl chloride was evaporated in vacuo and toluene
3. 3
   workup.ADDITIONwas added
4. 4
   기타Toluene was evaporated in vacuo

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.

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