Water → Gamma-Decalactone

HRID 599718

Reaction equation

HRID 599718 reaction equation
O=[C:2]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][CH2:4][C:5]([O:7]CC(C)C)=[O:6].[BH4-].[Na+].O.C(OCC)(=O)C>C(O)C>[CH3:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:2]1[O:7][C:5](=[O:6])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 252092612-Methylpropyl 4-oxodecanoate

Product 1

HCID 12813Gamma-Decalactone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

In 200 ml of 99.5% ethanol, was dissolved 24.2 g (0.10 mol) of isobutyl 4-oxodecanoate. Thereto was added 4.2 g (0.11 mol) of sodium borohydride in small quantities, and then the mixture was stirred for 10 minutes at 25° C. The solution was poured into 1 L of water, and 1 L of ethyl acetate was further added thereto followed by stirring to thereby extract the product into the ethyl acetate phase. Ethyl acetate was distilled off followed by vacuum distillation, yielding γ-decalactone (a compound in which R61 represents an n-pentyl group in the above formula (39)). Gas chromatographic analysis showed that the yield of γ-decalactone relative to isobutyl 4-oxodecanoate was 93%. In the resulting γ-decalactone, a plastic-like flavor or acid taste was not observed at all, but it had a good peach-like aroma.

Workup

  1. additionwas further added
  2. stirringby stirring
  3. extractionto thereby extract the product into the ethyl acetate phase
  4. distillationEthyl acetate was distilled off
  5. distillationfollowed by vacuum distillation

Sources & evidence

ORD record
ord-86533efc566141899f7c59d449285252
Source dataset
uspto-grants-2011_03
Patent number
US07897802B2

Linked notes

Loading…