Acetone → HCID 58972219, compound

HRID 922068Notes

Reaction equation

HRID 922068 reaction equation
Cl[CH2:2][CH2:3][CH2:4]/[C:5](/[CH3:21])=[CH:6]/[CH2:7][C:8]1[C:13]([CH3:14])=[C:12]([O:15][CH3:16])[C:11]([CH3:17])=[C:10]([CH3:18])[C:9]=1[O:19][CH3:20].[Na+].[I-:23].CC(C)=O>O>[I:23][CH2:2][CH2:3][CH2:4]/[C:5](/[CH3:21])=[CH:6]/[CH2:7][C:8]1[C:13]([CH3:14])=[C:12]([O:15][CH3:16])[C:11]([CH3:17])=[C:10]([CH3:18])[C:9]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 58972218HCID 58972218, compound

Product 1

HCID 58972219HCID 58972219, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(E)-1-(6-chloro-3-methylhex-2-enyl)-2,5-dimethoxy-3,4,6-trimethylbenzene (725.8 mg, 2.334 mmol) and NaI (3.09 g, 20.61 mmol) were dissolved into acetone (10 mL) and heated to reflux for 18 h. The reaction mixture was cooled to room temperature and the cloudy solution added to H2O (50 mL) and of a 50% EtOAc/hexanes solution (50 mL), the layers separated and the aqueous phase extracted with hexanes (3×25 mL), then MTBE (2×25 mL). The organics were combined and washed with saturated NaCl solution (2×25 mL) and dried over anhydrous Na2SO4. Concentration yielded 930.0 mg (99.0%) of 1-((E)-6-iodo-3-methylhex-2-enyl)-2,5-dimethoxy-3,4,6-trimethylbenzene as a pale yellow oil. 1H NMR (400 MHz, CDCl3) d 5.12 (t, J=6.4 Hz, 1H), 3.65 (s, 6H), 3.36 (d, J=6.0 Hz, 2H), 3.12 (t, J=7.2 Hz, 2H), 2.18 (S 9H), 2.07 (t, J=7.2 Hz, 2H), 1.91 (t, J=7.2 HZ, 2H), 1.77 (s, 3H), 13C NMR (100 MHz, CDCl3) d 153.1, 152.6, 133.0, 131.3, 128.4, 127.9, 127.6, 124.7, 60.9, 60.1, 40.1, 31.7, 26.1, 16.1, 12.8, 12.7, 12.2.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 h
  3. customthe layers separated
  4. extractionthe aqueous phase extracted with hexanes (3×25 mL)
  5. washwashed with saturated NaCl solution (2×25 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationConcentration

Sources & evidence

ORD record
ord-6b19434fd3804309b597e710c906b717
Source dataset
uspto-grants-2016_03
Patent number
US09278085B2

Reaction notes

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