HCID 20277066, compound → HCID 20277057, compound

HRID 1248611Notes

Reaction equation

HRID 1248611 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-e7474bb68e7c469892a769777b0f434d
Source dataset
uspto-grants-1985_06
Patent number
US04525361

Reaction notes

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