Iodine → HCID 22990510, compound

HRID 2049852Notes

Reaction equation

HRID 2049852 reaction equation
[Mg].[CH:2](Cl)([CH3:4])[CH3:3].II.[CH3:8][CH:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:10][CH:11]=[O:12]>CCOCC>[CH3:3][CH:2]([CH:11]([OH:12])[CH2:10][CH:9]([CH3:8])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH3:4]

Participants

6

Reactant 4

HCID 807IodineHCID 63612-Chloropropane2×HCID 892263,5-DimethylhexanalHCID 5462224Magnesium2×

Product 1

HCID 22990510HCID 22990510, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

26.4 g (1.1 gram atom) of magnesium shavings and 100 ml of dry ether are added to a round flask which is provided with a stirrer, condenser, thermometer and dropping funnel. There is now slowly added thereto a solution of 86.4 g (1.1 mol) of isopropyl chloride in 150 ml of anhydrous ether and the mixture is held at reflux temperature. The reaction is initiated by the addition of a small amount of iodine to the magnesium. After completion of the addition of the isopropyl chloride, the mixture is held for a further 1 hour at reflux temperature. There are now slowly added thereto at 5° C. 128.2 g (1 mol) of 3,5-dimethylhexanal dissolved in 250 ml of anhydrous ether. The mixture is again held for 3 hours at reflux temperature. The mixture is then cooled down to 0° C. and the product is decomposed by the addition of 340 ml of ice-cold 10% hydrochloric acid. The ethereal solution is washed neutral with water and dried, and the solvent is evaporated. There are thus obtained 176 g (70%) of crude product, fractional distillation of which yields 121.4 g of 2,5,7-trimethyl-octan-3-ol of boiling point 79° C./5 mmHg; nD20 =1.4362.

Workup

  1. customis provided with a stirrer, condenser
  2. additionThere is now slowly added
  3. temperatureat reflux temperature
  4. temperatureat reflux temperature
  5. additionThere are now slowly added
  6. customat 5° C
  7. waitThe mixture is again held for 3 hours
  8. temperatureat reflux temperature
  9. washThe ethereal solution is washed neutral with water
  10. customdried
  11. customthe solvent is evaporated
  12. distillation176 g (70%) of crude product, fractional distillation of which

Sources & evidence

ORD record
ord-e4e064ad112947b9af98d516d4609561
Source dataset
uspto-grants-1980_04
Patent number
US04198532

Reaction notes

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