4-Chlorophenol → 1-Chloro-4-(1,1-dimethyl-but-3-enyloxy)-benzene

HRID 885191

反応式

HRID 885191 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][C:10]1[C:11](=O)[C:12](C)=[CH:13]C(=O)[CH:15]=1.CC(OP(C1C=CC=CC=1)C1C=CC=CC=1)(CC=C)C>ClC(Cl)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]([CH3:15])([CH3:9])[CH2:11][CH:12]=[CH2:13])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 46844-ChlorophenolHCID 682412,6-Dimethyl-1,4-benzoquinoneHCID 59173107(2-Methyl-pent-4-en-2-oxy)diphenylphosphine

生成物 1

HCID 203571901-Chloro-4-(1,1-dimethyl-but-3-enyloxy)-benzene収率 2%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

反応条件

温度
0 °C

実験手順

To a cooled (0° C.), stirred mixture of 4-chloro-phenol (4.34 g) and 2,6-dimethylbenzoquinone (4.60 g) was added dropwise a solution of (2-methyl-pent-4-en-2-oxy)diphenylphosphine (8.0 g) in dichloroethane (20 ml). The mixture was then heated at 95° C. for 24 h. The reaction mixture was cooled to room temperature and concentrated in vacuo and the residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give 1-chloro-4-(1,1-dimethyl-but-3-enyloxy)-benzene (0.14 g, 2%) as a colourless oil. MS (EI): 171.1 ([{37Cl}M−C3H5−]+), 1691 ([{35Cl}M−C3H5]+).

後処理

  1. temperatureThe mixture was then heated at 95° C. for 24 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc)

出典と根拠

ORDレコード
ord-c15e42ad2639456eb37993d3fe98a7f6
出典データセット
uspto-grants-2012_08
特許番号
US08242153B2

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