Dimethyl Succinate → HCID 22460019, compound

HRID 2185140Notes

Reaction equation

HRID 2185140 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[C:13]([O:21][CH3:22])(=[O:20])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].CC(C)([O-])C.[K+].[C:29]([O-:32])(=[O:31])[CH3:30].[Na+]>C(OC(=O)C)(=O)C.Cl.CO>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:4]=1[CH:5]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=[C:13]2[O:31][C:29](=[O:32])[CH3:30].[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:4]=1[CH:5]=[C:14]([C:13]([O:21][CH3:22])=[O:20])[CH:15]=[C:16]2[OH:18]

Participants

9

Reactant 4

HCID 7820Dimethyl SuccinateHCID 691752,4-DimethoxybenzaldehydeHCID 517045Sodium AcetateHCID 23665647Potassium tert-butoxide

Product 2

HCID 22460019HCID 22460019, compoundHCID 22460020HCID 22460020, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 7918Acetic AnhydrideSolvent

Procedure

5,7-dimethoxy-3-methoxycarbonyl-1-acetoxynaphthalene is synthesized according to the procedure described in Org. React. 1951, 6, 1; by the reaction of 2,4-dimethoxybenzaldehyde and dimethyl succinate in the presence of potassium tert-butoxide followed by a cyclization in acetic anhydride in the presence of sodium acetate. 5,7-dimethoxy-3-methoxycarbonyl-1-naphthol is then obtained after deacetylation of the preceding product in HCl(2N)/methanol under reflux for 3 hours.

Workup

  1. customReact

Sources & evidence

ORD record
ord-5f837e0df9354e659b5fe55764f29cf3
Source dataset
uspto-grants-2002_06
Patent number
US06399791B1

Reaction notes

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