2-Methyl-6-methylene-7-octen-2-ol → 2,6,6-Trimethyl-2-vinyltetrahydropyran

HRID 358413Notes

Reaction equation

HRID 358413 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]([OH:30])([CH2:23][CH2:24][CH2:25][C:26]([CH:28]=[CH2:29])=[CH2:27])[CH3:22].CC(C)=CC(O)/C=C(/C=C)\C>>[CH3:27][C:26]1([CH:28]=[CH2:29])[CH2:25][CH2:24][CH2:23][C:21]([CH3:20])([CH3:22])[O:30]1

Participants

4

Reactant 3

HCID 109752-Methyl-6-methylene-7-octen-2-olHCID 11776TriphenylphosphineHCID 6430998HCID 6430998, compound

Product 1

HCID 5225142,6,6-Trimethyl-2-vinyltetrahydropyranYield 11.7%

Procedure

Example 12 was repeated except that only 0.105 g triphenylphosphine was used and 22.6 g of N,N-diethyl-7-hydroxygeranylamine was used as the amine. After 9 hours at 120° there was obtained a yield of 11.7% 2,6,6-trimethyl-2-vinyltetrahydropyran, 29.6% myrcenol, 22.2% cis and 17.3% trans-ocimenol.

Sources & evidence

ORD record
ord-9caecc1f57d44f2799fa1adb6dd0ad5b
Source dataset
uspto-grants-1984_08
Patent number
US04467118

Reaction notes

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