Hexane → 4,8-Dimethylnona-3,7-dien-2-ol

HRID 725772

Reaction equation

HRID 725772 reaction equation
C[Mg]Cl.[CH3:4][C:5](=[CH:7][CH2:8][CH2:9]/[C:10](=[CH:12]/[CH:13]=[O:14])/[CH3:11])[CH3:6].[NH4+].[Cl-].[CH3:17]CCCCC>COC(C)(C)C.O>[CH3:11][C:10]([CH2:9][CH2:8][CH:7]=[C:5]([CH3:4])[CH3:6])=[CH:12][CH:13]([OH:14])[CH3:17]

Participants

7

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 638011CitralHCID 178418332HCID 178418332, compound

Product 1

HCID 1068744,8-Dimethylnona-3,7-dien-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent2×

Conditions

Temperature
10 °C

Procedure

1 l of t-butyl methyl ether and 1.05 l of 3N methyl magnesium chloride solution were placed under N2 in a 41/2 l sulphonation flask having a thermometer, stirrer and dropping funnel and 456 g of geranial in 500 ml of t-butyl methyl ether were added dropwise at 0° C. The mixture was stirred at 10° C. for 1 hour and poured on to 3 kg of ice and 500 g of NH4Cl and treated with 1 l of hexane. After mixing well the H2O phase was separated and washed neutral 3 times with 500 ml of NH4Cl solution, dried and evaporated.

Workup

  1. customwas separated
  2. washwashed neutral 3 times with 500 ml of NH4Cl solution
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-f339ef21ee2f4548b11a6ee422594f82
Source dataset
uspto-grants-1998_01
Patent number
US05707961

Linked notes

Loading…