Acetic Acid → HCID 15830832, compound

HRID 382248Notes

Reaction equation

HRID 382248 reaction equation
[CH3:1][CH:2]([CH2:5][CH:6]([CH3:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:3]=[O:4].C(O)(=O)C.[BH4-].[Na+].O>CO.C(OC)(C)(C)C>[CH3:1][CH:2]([CH2:5][CH:6]([CH3:14])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:3][OH:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 15907301HCID 15907301, compound

Product 1

HCID 15830832HCID 15830832, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
20 °C

Procedure

Into a one liter flask equipped with a mechanical air stirrer, temperature probe, nitrogen inlet, autojack, and cooling bath was placed 50 mL methanol, 2,4-dimethyl-5-phenylpentanal (50.0 g, 0.26 mol), and acetic acid (11.0 g, 0.18 mol). To the stirred solution was added NaBH4 (70 g, 0.18 mol) in 50 mL of methanol over a period of two hours while maintaining the reaction temperature at 20° C. Water was then added until the all materials went into solution and 200 mL methyl t-butyl ether was then added. The organic phase was isolated, washed with three 50 mL portions of saturated NaCl solution, dried over magnesium sulfate, filtered, and rotovapped to give the product as a colorless liquid (49.9 g), odor—fresh, green herbal.

Workup

  1. customInto a one liter flask equipped with a mechanical air stirrer
  2. temperaturetemperature probe, nitrogen inlet, autojack, and cooling bath
  3. additionwas then added
  4. customThe organic phase was isolated
  5. washwashed with three 50 mL portions of saturated NaCl solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-eae41accab0143b9b18726ce0e17eb77
Source dataset
uspto-grants-2001_10
Patent number
US06310033B1

Reaction notes

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