Vanillin → (4R,5R)-2-(3-methoxy-4-hydroxy-phenyl)-4,5-dicarbomethoxy-1,3-dioxolane

HRID 1885396

Reaction equation

HRID 1885396 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[C:12]([C@@H:16]([C@H:18]([C:20]([O:22][CH3:23])=[O:21])[OH:19])O)([O:14][CH3:15])=[O:13]>CO>[CH3:7][O:6][C:5]1[CH:4]=[C:3]([CH:2]2[O:19][C@@H:18]([C:20]([O:22][CH3:23])=[O:21])[C@H:16]([C:12]([O:14][CH3:15])=[O:13])[O:1]2)[CH:11]=[CH:10][C:8]=1[OH:9]

Participants

4

Reactant 2

HCID 1183VanillinHCID 11851Dimethyl L-tartrate

Product 1

HCID 54460002(4R,5R)-2-(3-methoxy-4-hydroxy-phenyl)-4,5-dicarbomethoxy-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a fashion similar to that described for Example 3, vanillin and dimethyl L-tartrate were condensed to provide (4R,5R)-2-(3-methoxy-4-hydroxy-phenyl)-4,5-dicarbomethoxy-1,3-dioxolane, mp 88°-90° C., [α]D25 -35.1° (c, 0.1, methanol). 1H-NMR (CDCl3) δ7.20 (1H, d, J=1.8 Hz), 7.06 (1H, dd, J=1.8 Hz and 8.2 Hz), 6.19 (1H, d, J=8.2 Hz), 6.08 (1H,s), 5.82 (1H, s), 4.96 (1H, d, J=3.8 Hz), 4.85 (1H, d, J=3.8 Hz), 3.91 (3H,s), 3.87 (3H,s), 3.84 (3H,s). IR (film) 3450, 1750, 1600, 1510, 1460, 1430 cm-1. Ms m/e (% abundance) 313(2), 312(12), 253(40), 168(84), 151(100), 124(22), 109(14), 59(18).

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-62f9104401f74f5ea2863c2be8f4e68d
Source dataset
uspto-grants-1992_09
Patent number
US05144048

Linked notes

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