1-Chloro-3-methyl-2-butene → HCID 22026338, compound

HRID 1793233Notes

Reaction equation

HRID 1793233 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1O.[OH-:10].[K+].[CH2:12](Cl)[CH:13]=[C:14]([CH3:16])[CH3:15]>C1C=CC=CC=1>[CH3:1][C:2]1[C:3](=[O:10])[C:4]([CH3:8])([CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 104291-Chloro-3-methyl-2-buteneHCID 113352,6-DimethylphenolHCID 14797Potassium Hydroxide

Product 1

HCID 22026338HCID 22026338, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2,6-dimethylphenol (5.00 g, 41.0 mmol), powdered KOH (85%, 1.5 eq., 4.05 g, 61.5 mmol), prenyl chloride (85%, 1.2 eq., 6.05 g, 49.2 mmol) and (NBu4)HSO4 (50 mg) in benzene (50 ml) was stirred at 0° C. for 3 h. The green suspension was then poured on ice and extracted with pentane. The organic phase was washed with aqueous NaOH (32%), water and brine, dried (MgSO4) and concentrated in vacuo at room temperature. The yellow crude dienone was ca. 85% pure and was converted without further purification. 1H-NMR (400 MHz, CDCl3): 6.81-6.79 (m, 1H), 6.20-10 (m, 2H), 4.92-4.88 (m, 1H, 2′-H), 2.51 (dd, J=13.9, 7.7 Hz, 1H, 1′-Ha), 2.17 (dd, J=13.9, 7.2 Hz, 1H, 1′-Hb), 1.86 (s, 3H), 1.62 (s, 3H), 1.57 (s, 3H), 1.17 (s, 3H, 6-CH3) ppm.

Workup

  1. additionThe green suspension was then poured on ice
  2. extractionextracted with pentane
  3. washThe organic phase was washed with aqueous NaOH (32%), water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo at room temperature
  6. customwas converted without further purification

Sources & evidence

ORD record
ord-f7d02303c56544f8ad2d461477c161c2
Source dataset
uspto-grants-2006_07
Patent number
US07078570B2

Reaction notes

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