Citronellal → 3,7-Dimethylocta-2,6-Dienal

HRID 1877743Notes

Reaction equation

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

Participants

Reactant 2

HCID 7794Citronellal2×

HCID 444041beta-Cyclodextrin

Product 1

HCID 88433,7-Dimethylocta-2,6-Dienal

Procedure

Determination of enantiomeric excess and absolute configuration: the enantiomeric excess of citronellal was determined using a modified β-cyclodextrin capillary column (hydrodex-β-TBDAc, 25 m, 0.25 mm) temperature program: 40° C. hold 2 min, 4° C./min to 120° C., 1 min. hold, 20° C./min to 180° C., 3 min. hold. Retention times were as follows: (S)- and (R)-citronellal 19.84 and 19.97 min resp. The absolute configuration of citronellal was determined by coinjecting a commercially available reference sample with known absolute configuration.

Workup

custom4° C./min to 120° C., 1 min.
custom20° C./min to 180° C., 3 min.

Sources & evidence

ORD record: ord-1975f9e264cb4afa9ac9adbad497db86
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08313923B2

Reaction notes

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