Hydrochloric Acid → HCID 9942591, compound

HRID 395905Notes

Reaction equation

HRID 395905 reaction equation
C[Si](C)(C)Cl.[CH:6](=[O:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].Br[CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18].Cl>C(OCC)(=O)C.[Zn]>[OH:14][CH:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 454OctanalHCID 6397ChlorotrimethylsilaneHCID 95576Methyl 2-bromopropionate

Product 1

HCID 9942591HCID 9942591, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

At room temperature, a three-necked flask fitted with reflux condenser, internal thermometer, dropping funnel and stirrer was charged, under nitrogen protective gas, with 5.5 g of zinc powder (84 mmol) in 34 ml of ethyl acetate. After 1.6 ml of trimethylchlorosilane (12.5 mmol) had been added, the mixture was heated at 65° C. Following cooling to 60° C., 7.2 g of octanal (56 mmol) were added, and over the course of 4 min, 11.2 g of methyl 2-bromopropionate (67 mmol) were added dropwise, the temperature being maintained at 65° C. by external cooling. The mixture was then stirred at 60° C. for 5 min and, after cooling to 0° C., acidified with 40 ml of 2 N hydrochloric acid to a pH of 1 and stirred for 30 min. Excess zinc was removed by filtration and the organic phase separated. The organic phase was then stirred at 0° C. with 40 ml of 0.5 N hydrochloric acid and finally washed with 20 ml of saturated sodium hydrogen carbonate solution. Following phase separation and drying over sodium sulfate, the solvent was removed by distillation under reduced pressure. Methyl 3-hydroxy-2-methyldecanoate was obtained in a yield of 10.2 g (85% of theory) with a boiling point of 68° C. (0.04 mbar). The diastereomer ratio was 2:1.

Workup

  1. customAt room temperature, a three-necked flask fitted
  2. temperaturewith reflux condenser
  3. temperatureFollowing cooling to 60° C.
  4. temperaturethe temperature being maintained at 65° C. by external cooling
  5. temperatureafter cooling to 0° C.
  6. stirringstirred for 30 min
  7. customExcess zinc was removed by filtration
  8. customthe organic phase separated
  9. stirringThe organic phase was then stirred at 0° C. with 40 ml of 0.5 N hydrochloric acid
  10. washfinally washed with 20 ml of saturated sodium hydrogen carbonate solution
  11. customFollowing phase separation
  12. dry with materialdrying over sodium sulfate
  13. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-7a9db1492e9f47859d8ead411c159d43
Source dataset
uspto-grants-2003_08
Patent number
US06605716B2

Reaction notes

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