Sulfuric Acid → p-Menthane-3,8-diol

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 7794Citronellal2×

Product 1

HCID 556998p-Menthane-3,8-diol

Procedure

Citronellal is treated with aqueous sulfuric acid solution of 5 weight % (hereinafter referring to wt. %) in concentration at room temperature to cause the ring closure of citronellal. Then, after the reaction product is extracted with ether or toluene, para-menthane-3,8-diol is obtained by distilling the extract under reduced pressures (J. Am. Chem. Soc., 75, 2367 (1953), examined Japanese Patent Publication 3-80138 and U.S. Pat. No. 5,298,250).

Workup

extractionThen, after the reaction product is extracted with ether or toluene

Sources & evidence

ORD record: ord-72534ecc8b2147f6ac983dfbd5066caf
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05959161

Reaction notes

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