Hydrochloric Acid → 6-Undecanol

HRID 23799Notes

Reaction equation

HRID 23799 reaction equation
C([O:3][CH2:4][CH3:5])=O.O.Cl.[CH2:8]([Mg]Br)[CH2:9][CH2:10][CH2:11][CH3:12]>>[CH3:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:4]([OH:3])[CH2:5][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8025Ethyl formateHCID 178445865HCID 178445865, compound2×

Product 1

HCID 320456-Undecanol

Procedure

To the solution of n-pentylmagnesium bromide in tetrahydrofuran synthesized in Example 2, 162 mL (2.0 mol) of ethyl formate was added dropwise in a nitrogen atmosphere and the mixture was stirred overnight at room temperature. After careful addition of water, the reaction mixture was neutralized with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and thereafter concentrated to give 340.8 g of 6-undecanol.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-640100c177ee446b8592582724bee103
Source dataset
uspto-grants-2005_02
Patent number
US06852867B2

Reaction notes

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