3-Chloro-2-methyl-1-propene → 2,5,5,8-Tetramethylnona-1,6,7-trien-4-ol

HRID 483242Notes

Reaction equation

HRID 483242 reaction equation
CC(CC(O)C(C)(C)C=C=C)=C.[CH3:13][C:14](=[CH2:17])[CH2:15]Cl.[CH3:18][C:19]([CH3:27])([CH:22]=[C:23]=[C:24]([CH3:26])[CH3:25])[CH:20]=[O:21]>>[CH3:13][C:14]([CH2:15][CH:20]([OH:21])[C:19]([CH3:27])([CH3:18])[CH:22]=[C:23]=[C:24]([CH3:26])[CH3:25])=[CH2:17]

Participants

4

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 36994162,5,5-Trimethylocta-1,6,7-trien-4-olHCID 110946983,4-Hexadienal, 2,2,5-trimethyl-

Product 1

HCID 134564422,5,5,8-Tetramethylnona-1,6,7-trien-4-olYield 92%

Procedure

2,5,5,8-tetramethylnona-1,6,7-trien-4-ol (2b) was prepared as described for 2a from 8.72 g (0.36 mole) of Mg, 32.65 g (0.36 mole) of β-methylallyl chloride and 16.61 g (0.12 mole) of 1b. The work up resulted in 21.44 g (92%) of 2b. Bp. 61°-2° C./0.3 mm Hg, nD16 1.4810.

Workup

  1. custom2,5,5,8-tetramethylnona-1,6,7-trien-4-ol (2b) was prepared

Sources & evidence

ORD record
ord-a639dfa80baf4508a146b51a54faa398
Source dataset
uspto-grants-1986_03
Patent number
US04578484

Reaction notes

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