Ammonium Chloride → HCID 22114347, compound

HRID 565084Notes

Reaction equation

HRID 565084 reaction equation
[CH3:1][Mg]Cl.[CH3:4][C:5]1([CH3:14])[O:7][CH:6]1[CH2:8][CH2:9][C:10]([CH:12]=[CH2:13])=[CH2:11].[NH4+].[Cl-]>O1CCCC1.C(OC(C)C)(C)C>[CH3:4][C:5]([OH:7])([CH:6]([CH3:1])[CH2:8][CH2:9][C:10](=[CH2:11])[CH:12]=[CH2:13])[CH3:14]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 122371Oxirane, 2,2-dimethyl-3-(3-methylene-4-penten-1-yl)-HCID 178418332HCID 178418332, compound

Product 1

HCID 22114347HCID 22114347, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 7914Diisopropyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

1230 ml of a solution of CH3MgCl 3M in tetrahydrofurane (Fluka) was added to 26.5 g of CuBr (Fluka) in 11 of diisopropylether with stirring at 0° (bath temperature). After one night, the reaction mixture was cooled to −20° and 467 g of epoxymyrcene [2-(3,4-epoxy-4-methylpentyl)-1,3-butadiene] in 4 l of isopropylether were added dropwise. After the addition, the reaction mixture was warmed to room temperature. After 23 h the reaction was completed. After hydrolysis with a 15% NH4Cl-solution and washing with brine, the product was distilled to obtain 96.6% pure 2,3-dimethyl-6-methylene-7-octen-2-ol with a yield of 453.7 g (88%).

Workup

  1. waitAfter one night
  2. temperaturethe reaction mixture was cooled to −20°
  3. additionAfter the addition
  4. washwashing with brine
  5. distillationthe product was distilled

Sources & evidence

ORD record
ord-8b75feeb6235482986bc82d425480d78
Source dataset
uspto-grants-2001_01
Patent number
US06169212A

Reaction notes

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