Hydrochloric Acid → 2-Chloro-4-t-butylbenzyl alcohol

HRID 2052786노트

반응식

HRID 2052786 반응식
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].[H-].C([Al+]CC(C)C)C(C)C.Cl>ClCCl.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:9]=[CH:8][C:3]=1[CH2:4][OH:5]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 17859604Methyl 2-chloro-4-t-butylbenzoateHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 688990782-Chloro-4-t-butylbenzyl alcohol수율 51%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

The triflate compound (638 mg, 2 mmol) obtained in Step 1-2, palladium acetate (14 mg), 1,3-diphenylphosphinopropane (25 mg), methanol (4 ml) and triethylamine (0.6 ml) were dissolved in dimethylformamide (5 ml), and the obtained solution was stirred at 80° C. in carbon monoxide atmosphere for 16 hours. After leaving the reaction mixture to cool followed by the extraction with ethyl acetate/hexane and the purification by the silica gel column chromatography, methyl 2-chloro-4-t-butylbenzoate was obtained. The ester thus obtained was dissolved in dichloromethane (2 ml). 1 M solution (2.5 ml) of diisobutylaluminum hydride in toluene was added dropwise to the obtained solution at −78° C. in argon atmosphere, and the resulting solution was stirred at that temperature for 5 minutes. 0.5 M hydrochloric acid (20 ml) was added to the reaction mixture, and the temperature was elevated to room temperature. After the extraction with ethyl acetate followed by the purification by the silica gel column chromatography, 2-chloro-4-t-butylbenzyl alcohol (yield: 204 mg, 51%) was obtained.

후처리

  1. customwas elevated to room temperature
  2. extractionAfter the extraction with ethyl acetate
  3. customfollowed by the purification by the silica gel column chromatography

출처 및 근거

ORD 기록
ord-53c10d519c3a43b596916ca9642b3e49
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326701B2

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