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

HRID 1729910Notes

Reaction equation

HRID 1729910 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 three 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 three 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-3f7a01461f7c4dc599415b83907cadc5
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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