2-Chloropropane → HCID 54222836, compound

HRID 2049853Notes

Reaction equation

HRID 2049853 reaction equation
[Mg].[CH:2](Cl)([CH3:4])[CH3:3].[CH3:6][C:7]([CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:8][CH:9]=[O:10]>CCOCC>[CH3:3][CH:2]([CH:9]([OH:10])[CH:8]=[C:7]([CH3:6])[CH2:11][CH:12]([CH3:14])[CH3:13])[CH3:4]

Participants

5

Reactant 3

HCID 63612-ChloropropaneHCID 4914396HCID 4914396, compoundHCID 5462224Magnesium

Product 1

HCID 54222836HCID 54222836, compoundYield 72.6%

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 anhydrous 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 90.2 g (1.15 mol) of isopropyl chloride in 150 ml of ether. After completion of the addition, the mixture is held at reflux temperature for a further 1 hour. There are now added thereto at a temperature of 10° C. 126.2 g (1 mol) of 3,5-dimethyl-2-hexenal dissolved in 250 ml of anhydrous ether. The mixture is held at reflux temperature for 3 hours, then cooled down to 0° C. and decomposed by the addition of 370 ml of 10% ice-cold hydrochloric acid. The ethereal solution is washed neutral with water and dried, and the solvent is evaporated. There are thus obtained 168 g of crude material, fractional distillation of which yields 123.7 g (72.6%) of 2,5,7-trimethyl-4-octen-3-ol of boiling point 78°-79° C./5 mmHg; nD20 =1.4526.

Workup

  1. customis provided with a stirrer, condenser
  2. additionThere is now slowly added
  3. additionAfter completion of the addition
  4. temperatureat reflux temperature for a further 1 hour
  5. additionThere are now added
  6. customat a temperature of 10° C
  7. temperatureat reflux temperature for 3 hours
  8. washThe ethereal solution is washed neutral with water
  9. customdried
  10. customthe solvent is evaporated
  11. distillation168 g of crude material, fractional distillation of which

Sources & evidence

ORD record
ord-f1bc666dde2b4f79af88189276fe8e82
Source dataset
uspto-grants-1980_04
Patent number
US04198532

Reaction notes

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