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

HRID 1939328

반응식

HRID 1939328 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
60 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-eb00a51ed22e454093eae96051f2121a
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05696146

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