HCID 12824119, compound → 2,3,5-Trimethyl-6-(6'-hydroxyhexyl)-hydroquinone

HRID 1248613Notes

Reaction equation

HRID 1248613 reaction equation
[CH3:1][C:2]1[C:3](=[O:21])[C:4]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](OCC)=[O:17])=[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][CH2:14][CH2:15][CH2:16][OH:17])[C:3]=1[OH:21]

Participants

4

Reactant 2

HCID 12824119HCID 12824119, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 202770692,3,5-Trimethyl-6-(6'-hydroxyhexyl)-hydroquinone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2,3,5-trimethyl-6-(5'-ethoxycarbonylpentyl)-1,4-benzoquinone (formula I-2 wherein R=H3C, n=4, in the form of ethylester) (0.1 part) in diethyl ether (10 volume parts) was treated with lithium aluminum hydride in the same manner as Example 53 to give 2,3,5-trimethyl-6-(6'-hydroxyhexyl)-hydroquinone (formula III-2 wherein R=H3C, n=4, in the free form). The product was treated with ferric chloride in the same manner as Example 53 and then crystallized from diethyl ether. The procedure provided 2,3,5-trimethyl-6-(6'-hydroxyhexyl)-1,4-benzoquinone (formula IV-2, wherein R=H3C, n=4 in the free form) as yellow needles melting at 43°-45° C.

Sources & evidence

ORD record
ord-12d332a6c36c435ea28d9e24ad9d21f8
Source dataset
uspto-grants-1985_06
Patent number
US04525361

Reaction notes

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