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

HRID 483241Notes

Reaction equation

HRID 483241 reaction equation
[CH3:1][C:2](=[CH2:5])[CH2:3]Cl.[CH3:6][C:7]([CH3:13])([CH:10]=[C:11]=[CH2:12])[CH:8]=[O:9].[NH4+].[Cl-]>CCOCC>[CH3:1][C:2]([CH2:3][CH:8]([OH:9])[C:7]([CH3:13])([CH3:6])[CH:10]=[C:11]=[CH2:12])=[CH2:5]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 25517Ammonium ChlorideHCID 776782,2-Dimethyl-3,4-pentadienal

Product 1

HCID 36994162,5,5-Trimethylocta-1,6,7-trien-4-olYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
15 °C

Procedure

300 ml of absolute ether were added to 7.29 g (0.30 mole) of dry Mg, the mixture was cooled to 15±1° C., and 27.19 g (0.30 mole) freshly distilled β-methylallyl chloride were added. The mixture was stirred over night at the same temperature. The white suspension was cooled to 0° C., and 11.03 g (0.10 mole) 1a in 150 ml absolute ether were added dropwise during 1 hour. The mixture was stirred at 0° C. for 4 hours (reaction monitored on GC). 37 ml of saturated NH4Cl solution were added with vigorous stirring. The solution was decanted from the magnesium salts which were washed several times with ether. The combined ether phases were dried (MgSO4). Distillation gave 14.22 g (91%) 2a, b.p. 60°-1° C./1.5 mm Hg.

Workup

  1. temperatureThe white suspension was cooled to 0° C.
  2. stirringThe mixture was stirred at 0° C. for 4 hours
  3. custom(reaction monitored on GC)
  4. customThe solution was decanted from the magnesium salts which
  5. washwere washed several times with ether
  6. dry with materialThe combined ether phases were dried (MgSO4)
  7. distillationDistillation

Sources & evidence

ORD record
ord-f7c6d9ae663c4a18aefa7d835ca2caef
Source dataset
uspto-grants-1986_03
Patent number
US04578484

Reaction notes

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