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

HRID 1939328Notes

Reaction equation

[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

Participants

Conditions

Temperature: 60 °C

Procedure

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)+.

Workup

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

Sources & evidence

ORD record: ord-eb00a51ed22e454093eae96051f2121a
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05696146

Reaction notes

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