Citronellol → Tetrahydro-pseudo-ionone

HRID 1283520Notes

Reaction equation

[CH3:1][C:2]([OH:16])([CH2:5][CH2:6][CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])C#C.CC(=CCCC(CCO)C)C.P(Cl)(Cl)Cl.P(Br)(Br)Br.C(OCC)(=O)CC(C)=O>>[CH3:15][CH:8]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:13])[CH3:14])[CH2:7][CH2:6][CH2:5][C:2](=[O:16])[CH3:1]

Participants

Reactant 5

HCID 8842Citronellol

HCID 8868Ethyl Acetoacetate

HCID 24387Phosphorus trichloride

HCID 24614Phosphorus tribromide

HCID 215184373,7,11-Trimethyldodeca-1-yn-10-en-3-ol

Product 1

HCID 102604Tetrahydro-pseudo-ionone

Procedure

3,7,11-trimethyldodeca-1-yn-10-en-3-ol can easily be synthesized by halogenating citronellol, which is used as a perfume, with phosphorus trichloride or phosphorus tribromide, reacting the halogenation product with ethyl acetoacetate to form 6,10-dimethylundeca-9-en-2-one, and subjecting it to ethynylation in the same manner as described above.

Sources & evidence

ORD record: ord-02b6a660d99641a1a82b86e9d2b0bfb2
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03975451

Reaction notes

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