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

HRID 358414Notes

Reaction equation

HRID 358414 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].C/C(/C=C)=C/CCC(O)(C)C.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

5

Reactant 4

HCID 109752-Methyl-6-methylene-7-octen-2-olHCID 11776TriphenylphosphineHCID 6430998HCID 6430998, compoundHCID 13547825(5Z)-2,6-Dimethyl-5,7-octadien-2-ol

Product 1

HCID 5225142,6,6-Trimethyl-2-vinyltetrahydropyranYield 13.1%

Procedure

Example 13 was repeated except that 0.210 g triphenylphosphine was used and 22.6 g N,N-diethyl-7-hydroxynerylamine. After 171/2 hours at 120° C. there was obtained a yield of 13.1% 2,6,6-trimethyl-2-vinyltetrahydropyran, 28.6% myrcenol, 16.1% cis-ocimenol, 21.9% trans-ocimenol.

Sources & evidence

ORD record
ord-3b49818c71524a84a86a8dab25ca3cd1
Source dataset
uspto-grants-1984_08
Patent number
US04467118

Reaction notes

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