p-Toluenesulfonic acid → HCID 15346017, compound

HRID 2393685Notes

Reaction equation

HRID 2393685 reaction equation
CC1(C)OC(=O)CC(=O)O1.C(O)CCCCCO.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22](S(O)(=O)=O)=[CH:21][CH:20]=1.[C:30]([O:43]CCCCCCO)(=[O:42])[CH2:31][C:32]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][OH:41])=[O:33].C(O)(=O)C.[NH:55]1[CH2:60][CH2:59]C[CH2:57][CH2:56]1>O.CC(C)=O>[OH:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][O:34][C:32]([C:31]1[C:30](=[O:42])[O:43][C:24]2[C:19]([CH:29]=1)=[CH:20][CH:21]=[C:22]([N:55]([CH2:60][CH3:59])[CH2:56][CH3:57])[CH:23]=2)=[O:33]

Participants

8

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 123741,6-HexanediolHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 9793820Piperidine, acetateHCID 20663734HCID 20663734, compound

Product 1

HCID 15346017HCID 15346017, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

In this scheme, bis-(6-hydroxyhexyl) malonate is first produced by reacting the Meldrum's acid and 1,6-hexanediol in the presence of catalytic quantities of p-toluenesulphonic acid with elimination of acetone and water. The bis-(6-hydroxyhexyl) malonate is then combined with 4-diethylaminosalicylic aldehyde in the presence of catalytic quantities of piperidine acetate to form the desired 3-(6-hydroxyhexoxycarbonyl)-7-diethylaminocoumarin.

Sources & evidence

ORD record
ord-b97699b8db47400494c7b8567fae1863
Source dataset
uspto-grants-1998_09
Patent number
US05807945

Reaction notes

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