HCID 20277066, compound → HCID 20277057, compound

HRID 1390585Notes

Reaction equation

HRID 1390585 reaction equation
[CH3:1][C:2]1[C:3](=[O:18])[C:4]([CH2:11][CH2:12][C:13](OCC)=[O:14])=[C:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([OH:9])[C:5]([CH3:10])=[C:4]([CH2:11][CH2:12][CH2:13][OH:14])[C:3]=1[OH:18]

Participants

4

Reactant 2

HCID 20277066HCID 20277066, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20277057HCID 20277057, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2,3,5-trimethyl-6-(2'-ethoxycarbonylethyl)-1,4-benzoquinone (formula I-2 wherein R=H3C, n=1, in the form of ethyl ester) (0.39 part) in diethyl ether (50 volume parts) was treated with lithium aluminum hydride in the same manner as Example 53 to give 2,3,5-trimethyl-6-(3'-hydroxypropyl)-hydroquinone (formula III-2 wherein R=H3C, X=Y=OH, n=1 in the free form). The product was treated with ferric chloride in the same manner as Example 53 and then subjected to column chromatography on silica gel and eluted with chloroform. The procedure provided 2,3,5-trimethyl-6-(3'-hydroxypropyl)-1,4-benzoquinone (formula IV-2 wherein R=H3C, n=1, in the free form) (0.25 part) as a yellow oil.

Sources & evidence

ORD record
ord-a4e4ad47383b4b148241eaabf3ab1578
Source dataset
uspto-grants-1979_02
Patent number
US04139545

Reaction notes

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