Sulfuric Acid → p-Menthane-3,8-diol

HRID 619769Notes

Reaction equation

[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][CH:7]([CH2:9][CH:10]=[O:11])[CH3:8])[CH3:3].S(=O)(=O)(O)[OH:13]>>[CH:7]1([CH3:8])[CH2:6][CH2:5][CH:4]([C:2]([OH:13])([CH3:3])[CH3:1])[CH:10]([OH:11])[CH2:9]1

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 7794Citronellal

Product 1

HCID 556998p-Menthane-3,8-diol

Procedure

The above-mentioned problems are resolved by the production method of this invention wherein citronellal is treated with aqueous sulfuric acid solution of 0.02 to 1.0 wt. % in concentration to produce para-menthane-3,8-diol. In case of recovering the produced para-menthane-3,8-diol, a method is preferably adopted, wherein after the reaction product is extracted with an aliphatic hydrocarbon solvent of 5 to 8 in carbon number, the extract is cooled down at temperature higher than the melting point of said aliphatic hydrocarbon solvent and of -10° C. or less to crystallize para-menthane-3,8-diol.

Sources & evidence

ORD record: ord-96e3dc476bdc4afb8d06a2e2a1ca41ae
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05959161

Reaction notes

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