Hydrochloric Acid → 3-(3,4-Dichlorophenyl)-2-propene-1-ol acetate

HRID 357238

反応式

HRID 357238 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8].N1C=CC=CC=1.[CH3:19][C:20](Cl)=[O:21].Cl>C(Cl)Cl.CN(C1C=CC=CN=1)C>[C:20]([O:12][CH2:11][CH:10]=[CH:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)(=[O:21])[CH3:19]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 537091912-Propen-1-ol, 3-(3,4-dichlorophenyl)-

生成物 1

HCID 538528443-(3,4-Dichlorophenyl)-2-propene-1-ol acetate収率 97%

試薬・触媒・溶媒 2

HCID 218852-Dimethylaminopyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
23 °C

実験手順

Treat a solution of the product of step 2 (13.2 g, 65 mmol) in CH2Cl2 (250 mL) at 0° C. with pyridine (7.89 mL, 97.5 mmol, 1.5 eq) and dimethylaminopyridine (397 mg, 3.25 0.05 eq), followed by CH3COCl (6.48 mL, 74.75 mmol, 1.15 eq). Allow the mixture to warm to 23° C., pour into 1M HCl (100 mL) and wash the resulting organic layer again with 1 M HCl (100 mL), followed by water (5×100 mL; pH=6.5-7). Dry the organic layer (Na2SO4) and concentrate to obtain 15.4 g (62.9 mmol, 97%) of 3-(3,4-dichlorophenyl)-2-propene-1-ol acetate as a colorless oil.

後処理

  1. washwash the resulting organic layer again with 1 M HCl (100 mL)
  2. dry with materialDry the organic layer (Na2SO4)
  3. concentrationconcentrate

出典と根拠

ORDレコード
ord-596ba5ac38d843dda8fd994e96809546
出典データセット
uspto-grants-1998_11
特許番号
US05840725

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