Methyl iodide → HCID 22400620, compound

HRID 260812Notes

Reaction equation

HRID 260812 reaction equation
[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[C:7]([CH3:11])[CH:6]=[CH:5][C:4]=1[C:12]1[O:13]C(C)(C)CN=1)[CH3:2].CI.[OH-:21].[K+]>CS(C)=O.O>[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[C:7]([CH3:11])[CH:6]=[CH:5][C:4]=1[C:12]([OH:13])=[O:21])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 22400614HCID 22400614, compound

Product 1

HCID 22400620HCID 22400620, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2-(2-Ethyl-3-methoxy-4-methylphenyl)-5,5-dimethyloxazoline, synthesized in like manner according to EXAMPLE 10, (2.7 g, 13.1 mmoles) and 2.2 mL (35.3 mmoles) of methyl iodide were dissolved in 4 mL of dimethyl sulfoxide. The resultant mixture was stirred for 18 hours at room temperature. A solution of 4.2 g of potassium hydroxide in 35 mL of water was added, and the mixture was heated at reflux for 8 hours. About 40 g ice was added, and the solution was extracted with ether. The aqueous layer was cooled on ice and acidified with 5% hydrochloric acid. The resulting precipitate was filtered and air-dried to yield 1.69 g of product. 1H NMR (200 MHz, CDCl3), δ=7.72 (1H, d, 8 Hz), 7.1 (1H, d, 8 Hz), 3.77 (3H, s), 3.06 (2H, q, 7 Hz), 2.36 (3H, s), 1.22 (3H, t, 7 Hz) ppm.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 8 hours
  3. extractionthe solution was extracted with ether
  4. temperatureThe aqueous layer was cooled on ice
  5. filtrationThe resulting precipitate was filtered
  6. customair-dried

Sources & evidence

ORD record
ord-0a4ef76c493a433eb375b3385d95dab1
Source dataset
uspto-grants-1996_06
Patent number
US05530028

Reaction notes

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