Hydrochloric Acid → HCID 14197812, compound

HRID 1946231Notes

Reaction equation

HRID 1946231 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH3:10][C:11](=[CH2:14])[CH:12]=[O:13].Cl>C(OCC)C.BrCCCCCCC>[CH3:14][C:11]([CH:12]([OH:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[CH2:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6562MethacroleinHCID 123691-BromoheptaneHCID 5462224Magnesium

Product 1

HCID 14197812HCID 14197812, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 123691-BromoheptaneCatalystHCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

Under an atmosphere of nitrogen the reaction flask is charged with 9.85 g magnesium and 100 ml diethyl ether. The Grignard reaction is started with 3.00 g bromo-heptane. Then a solution of 70.00 g bromo-heptane in 50 ml diethyl ether is added dropwise within 90 minutes, the reaction mixture is kept at mild reflux and subsequently cooled to 0° C. to add now within 30 minutes a solution of 28.70 g 2-methyl-2-propenal in 30 ml diethyl ether. After further stirring for 2 hours at room temperature the reaction mixture is again cooled to 0° C. and 50 ml of diluted hydrochloric acid (3.5%) are carefully added. The organic layer is washed with water, dried with sodium sulfate and subsequently concentrated to give 86.7 g crude material. Distillation over a 10 cm-column (Widmer type) gives 40.5 g 2-methyl-1-decen-3-ol having a boiling point of 75° C. at 0.12 bar.

Workup

  1. customThe Grignard reaction
  2. temperatureat mild reflux
  3. temperatureis again cooled to 0° C.
  4. washThe organic layer is washed with water
  5. dry with materialdried with sodium sulfate
  6. concentrationsubsequently concentrated
  7. customto give 86.7 g crude material
  8. distillationDistillation over a 10 cm-column (Widmer type)

Sources & evidence

ORD record
ord-a1fca326c2c74ce18b1a290add80d826
Source dataset
uspto-grants-2013_03
Patent number
US08399399B2

Reaction notes

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