Hydroxycitronellal → Citronellol

HRID 1438774Notes

Reaction equation

HRID 1438774 reaction equation
O[CH2:2]/[C:3](=[CH:5]\[CH2:6][CH2:7][CH:8]([CH2:10][CH2:11][OH:12])[CH3:9])/[CH3:4].CC(CC=O)CCCC(O)(C)C.CC(=CCC/C(=C/CO)/C)C.OC/C=C(/C)\CCC=C(C)C.CC1(C)C2CC1CCC2=C.CC(C)=CCCC(C=C)=C.Cl>>[CH3:2][C:3](=[CH:5][CH2:6][CH2:7][CH:8]([CH2:10][CH2:11][OH:12])[CH3:9])[CH3:4]

Participants

7

Reactant 6

HCID 7888HydroxycitronellalHCID 14896Beta-PineneHCID 637566GeraniolHCID 643820NerolHCID 19805005Myrcene hydrochlorideHCID 77134639(Z)-2,6-dimethyloct-2-ene-1,8-diol

Product 1

HCID 8842Citronellol

Procedure

A primary use for hydroxycitronellol is as an intermediate in the synthesis of hydroxycitronellal, (7-hydroxy-3,7-dimethyloctan-1-al), a widely used perfumery material. Conventionally, in this synthesis, a mixture of geraniol and nerol is prepared from beta-pinene via myrcene hydrochloride and is partially hydrogenated to produce citronellol. Citronellol is then hydrated under acid conditions to produce hydroxycitronellol. It has also been made from myrcene by preparing the dihydrochloride and then chlorodihydrogeranyl acetate, followed by saponification and hydrogenation.1

Workup

  1. customConventionally, in this synthesis

Sources & evidence

ORD record
ord-d9fcde7c0b9e46e8aed934fd9f036ca6
Source dataset
uspto-grants-1977_11
Patent number
US04056573

Reaction notes

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