Water → 2-[4-(2,2-Dimethylbenzo[d]1,3-dioxolan-5-oxy)butoxy]-1,3-dichloro-5-(phenylmethoxy)benzene

HRID 731969

反応式

HRID 731969 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([Cl:16])[C:3]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21]Cl.[CH3:23][C:24]1([CH3:34])[O:28][C:27]2[CH:29]=[CH:30][CH:31]=[C:32](O)[C:26]=2[O:25]1.C(=O)([O-])[O-:36].[K+].[K+].O>CN(C=O)C>[CH3:23][C:24]1([CH3:34])[O:28][C:27]2[CH:29]=[CH:30][C:31]([O:36][CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:3]3[C:4]([Cl:16])=[CH:5][C:6]([O:8][CH2:9][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)=[CH:7][C:2]=3[Cl:1])=[CH:32][C:26]=2[O:25]1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 62765Bendiocarb phenolHCID 222571231,3-Dichloro-2-(4-chlorobutoxy)-5-(phenylmethoxy)benzene

生成物 1

HCID 689998862-[4-(2,2-Dimethylbenzo[d]1,3-dioxolan-5-oxy)butoxy]-1,3-dichloro-5-(phenylmethoxy)benzene収率 71.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A stirred solution of 0.3 gram (0.00083 mole) of 1,3-dichloro-2-(4-chlorobutoxy)-5-(phenylmethoxy)benzene, 0.17 gram (0.00100 mole) of 2,2-dimethylbenzo[d]1,3-dioxolan-4-ol, and 0.17 gram (0.00125 mole) of potassium carbonate in 10 mL of DMF was heated at 80° C. for about 18 hours. After this time, the reaction mixture was cooled and 30 mL of water was added. The mixture was then extracted with three 20 mL portions of diethyl ether. The combined extracts were washed with 20 mL of an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using 1:1 methylene chloride:hexane as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.29 gram of the subject compound. The NMR spectrum was consistent with the proposed structure.

後処理

  1. temperatureAfter this time, the reaction mixture was cooled
  2. extractionThe mixture was then extracted with three 20 mL portions of diethyl ether
  3. washThe combined extracts were washed with 20 mL of an aqueous solution saturated with sodium chloride
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a residue
  7. customThe residue was purified with column chromatography on silica gel using 1:1 methylene chloride
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-59a35a2f9bb440a88ac7a187a0b59c5c
出典データセット
uspto-grants-2009_09
特許番号
US07585891B2

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