Acetone → 5-{4-[2-Hydroxy-4-hydroxyimino-2-methyl-4-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)butoxy]benzyl}-2,4-dioxothiazolidine

HRID 1885234Notes

Reaction equation

HRID 1885234 reaction equation
[OH:1][C:2]1[C:3]([CH3:33])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][C:5]2=[N:31][OH:32].Cl.CC(C)=[O:37]>>[OH:8][C:7]([CH3:14])([CH2:6][C:5](=[N:31][OH:32])[C:4]1[C:9](=[O:37])[C:10]([CH3:13])=[C:11]([CH3:12])[C:2](=[O:1])[C:3]=1[CH3:33])[CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric Acid2×HCID 867461085-[4-(6-Hydroxy-4-hydroxyimino-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2,4-dioxothiazolidine

Product 1

HCID 867461075-{4-[2-Hydroxy-4-hydroxyimino-2-methyl-4-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)butoxy]benzyl}-2,4-dioxothiazolidine

Procedure

The procedure of Example 1 was repeated, but using 2 g of 5-[4-(6-hydroxy-4-hydroxyimino-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2,4-dioxothiazolidine, 15 ml of acetone and 5 ml of an aqueous solution of ferric chloride acidified with hydrochloric acid (a mixture of about 65% by weight of FeCl3.6H2O and about 35% by weight of concentrated hydrochloric acid), to afford 0.74 g of the title compound as a yellow powder softening at 80°-85° C.

Sources & evidence

ORD record
ord-066c1ee7dc774a52b7da69ee2c310669
Source dataset
uspto-grants-1992_09
Patent number
US05143930

Reaction notes

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