2,3-Dimethoxy-1,4-naphthoquinone → HCID 20403098, compound

HRID 2164720Notes

Reaction equation

HRID 2164720 reaction equation
CO[C:3]1[C:4](=[O:16])[C:5]2[C:10]([C:11](=[O:15])[C:12]=1[O:13][CH3:14])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:17]1[CH2:21]O[CH2:19][CH2:18]1>[Cl-].[Cl-].[Zn+2]>[CH3:14][O:13][C:12]1[C:11](=[O:15])[C:10]2[C:5]([C:4](=[O:16])[C:3]=1[CH2:19][CH2:18][CH2:17][CH2:21][CH2:5][CH2:4][CH2:3][CH2:12][CH2:11][CH2:10][CH2:9][CH3:8])=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

4

Reactant 2

HCID 31362,3-Dimethoxy-1,4-naphthoquinoneHCID 8028Tetrahydrofuran2×

Product 1

HCID 20403098HCID 20403098, compoundYield 13.4%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To 0.64 g (4.71 mmoles) of ZnCl2 in 50 mL of THF was added 7.0 g (0.697 mmoles/g in THF, 4.88 mmoles) of dodecyl MgBr. This mixture was added dropwise to 1.00 g (4.67 mmoles) of 2,3-dimethoxy-1,4-naphthoquinone in 50 mL of THF. The mixture was stirred overnight and worked up as in Example 30. Thus, 0.223 g (0.626 mmoles, 13.4%) of 2-methoxy-3-dodecyl-1,4-naphthoquinone was obtained, mp: 61° to 63° C. 1H NMR (δ, CDCl3): 8.05 (m,2H), 7.65 (m,2H), 4.10 (s,3H), 2.55 (m,2H), 1.30 (br s,20H), 0.85 (m,3H). IR (cm-1, KBr): 2950w, 2918s, 2842m, 1666s, 1642m, 1608m, 1589m, 1571w, 1462m, 1338m, 1329m, 1261m, 1255w, 1209m.

Sources & evidence

ORD record
ord-a0853f3b723b43369a470ada16432129
Source dataset
uspto-grants-1985_03
Patent number
US04507241

Reaction notes

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