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

HRID 1867244ノート

反応式

HRID 1867244 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 688990782-Chloro-4-t-butylbenzyl alcohol収率 51%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-aa52a292ef064753baa62f02516e13db
出典データセット
uspto-grants-2009_12
特許番号
US07632830B2

反応ノート

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