p-Toluenesulfonic acid → Methyl(2,2-di[4-chlorophenyl]-1,3-benzodioxolan-5-yl)acetate

HRID 1939328ノート

反応式

HRID 1939328 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)([O:11][CH3:12])[O:9][CH3:10])=[CH:4][CH:3]=1.O[C:21]1[CH:22]=[C:23]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:24]=CC=1O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:32][O:31][C:29](=[O:30])[CH2:28][C:23]1[CH:22]=[CH:21][C:12]2[O:11][C:8]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[O:9][C:10]=2[CH:24]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 11008556Methyl 3,4-DihydroxyphenylacetateHCID 11652307Benzene, 1,1'-(dimethoxymethylene)bis[4-chloro-

生成物 1

HCID 54378343Methyl(2,2-di[4-chlorophenyl]-1,3-benzodioxolan-5-yl)acetate収率 37.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

A mixture of di(4-chlorophenyl)dimethoxymethane (26 g) (see Preparation 13) and methyl (3,4-dihydroxyphenyl)acetate (16 g) (see Preparation 12) in toluene (200 ml) was heated under reflux in a Dean-Stark apparatus for one hour. The reaction was cooled to 60° C. and p-toluenesulphonic acid was added (50 mg). After heating under reflux for 16 hours the solution was cooled, washed with aqueous sodium bicarbonate (100 ml), dried (MgSO4) and evaporated to a brown gum. Flash chromatography (silica, eluant=4:1 hexane/ethyl acetate) gave the title compound as a pale yellow gum (13.7 g). LRMS m/z=415(m)+.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux in a Dean-Stark apparatus for one hour
  3. temperatureAfter heating
  4. temperatureunder reflux for 16 hours the solution
  5. temperaturewas cooled
  6. washwashed with aqueous sodium bicarbonate (100 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated to a brown gum

出典と根拠

ORDレコード
ord-eb00a51ed22e454093eae96051f2121a
出典データセット
uspto-grants-1997_12
特許番号
US05696146

反応ノート

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