Methyl iodide → 1-Chloro-4-hydroxy-4-methylnonane

HRID 372513Notes

Reaction equation

HRID 372513 reaction equation
I[CH3:2].[Mg].[Cl:4][CH2:5][CH2:6][CH2:7][C:8](=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>CCOCC>[Cl:4][CH2:5][CH2:6][CH2:7][C:8]([OH:14])([CH3:2])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5462224MagnesiumHCID 203861031-Chlorononan-4-one

Product 1

HCID 203276741-Chloro-4-hydroxy-4-methylnonane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The Grignard reagent prepared from iodomethane (14.2 g., 0.1 mole) and magnesium (2.4 g., 0.1 mole) in ether solution is added, dropwise to an ether solution of 1-chloro-4-nonanone (Example A, Step 1) (17.6 g., 0.1 mole). The reaction is refluxed gently for 3 hours then cooled and poured carefully into ice water (300 ml.). The ether layer is separated, washed with brine, and dried over sodium sulfate. Removal of the ether in vacuo gives 1-chloro-4-hydroxy-4-methylnonane as an oil. The tertiary alcohol is dissolved in pyridine and treated with one molar equivalent of acetic anhydride at 60°-80° for 8-16 hours to give 1-chloro-4-acetoxy-4-methylnonane as a colorless oil.

Workup

  1. temperatureThe reaction is refluxed gently for 3 hours
  2. temperaturethen cooled
  3. customThe ether layer is separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the ether in vacuo

Sources & evidence

ORD record
ord-a4f64b3c28be47ca858b05b1bd20ab82
Source dataset
uspto-grants-1978_05
Patent number
US04091107

Reaction notes

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