Hydrochloric Acid → gamma-methyl-gamma-n-propyl-delta-Valerolactone

HRID 1577474Notes

Reaction equation

HRID 1577474 reaction equation
[C:1]([CH2:3][CH2:4][C:5]([CH3:11])([CH2:8][CH2:9][CH3:10])[CH:6]=[O:7])#N.[OH-:12].[K+].[BH4-].[Na+].Cl>CCOCC.O>[CH3:11][C:5]1([CH2:8][CH2:9][CH3:10])[CH2:6][O:7][C:1](=[O:12])[CH2:3][CH2:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 4311764Sodium borohydrideHCID 149931194-Formyl-4-methylheptanenitrile

Product 1

HCID 20570604gamma-methyl-gamma-n-propyl-delta-Valerolactone

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 50 g. (0.326 mole) of 2-(beta-cyanoethyl) 2-methylpentanal, 27.3 g. (0.489 mole) potassium hydroxide and 150 ml. water was stirred for four and a half hours at reflux temperature. The reaction mixture was cooled to 20° C. and a solution of 13.6 g. (0.359 mole) sodium borohydride in 75 ml. water was added. The reaction temperature rose to 50° C. Stirring was continued for one and a half hours during which period the temperature dropped to 20° C. again. The reaction mixture was acidified with dilute hydrochloric acid. The oil was taken up in ether, washed with water and dried. Distillation yield 39.5 g. (78%) γ-methyl-γ-propyl-δ-valerolactone boiling at 85°-86° C. at 0.6 mm; nD20 1.4599. This oil exhibits a greenish, cumarinic, coconut-like hairy odor.

Workup

  1. additionA mixture of 50 g
  2. temperatureat reflux temperature
  3. customrose to 50° C
  4. waitwas continued for one and a half hours during which period
  5. additionthe temperature dropped to 20° C. again
  6. washwashed with water
  7. customdried
  8. distillationDistillation yield 39.5 g

Sources & evidence

ORD record
ord-c19bdeab1a334a758e0cfa4501ad88e9
Source dataset
uspto-grants-1981_09
Patent number
US04288350

Reaction notes

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