p-Toluenesulfonic acid → HCID 15346017, compound

HRID 1067166Notes

Reaction equation

HRID 1067166 reaction equation
CC1(C)[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])O1.[CH2:11]([OH:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22](S(O)(=O)=O)=[CH:21][CH:20]=1.OCCCCCCC(CCCCCCO)(C([O-])=O)C([O-])=O.C(O)(=O)C.[NH:55]1[CH2:60][CH2:59]C[CH2:57][CH2:56]1>O.CC(C)=O>[OH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:18][C:4]([C:6]1[C:7](=[O:8])[O:9][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:5]

Participants

8

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 123741,6-HexanediolHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 9793820Piperidine, acetateHCID 21192291HCID 21192291, 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-toluene-sulphonic 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-7ed2dc310e91405cbedd542a89e52d48
Source dataset
uspto-grants-2001_06
Patent number
US06248457B1

Reaction notes

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