Binap, (A+-)- → Citronellic acid

HRID 1088490Notes

Reaction equation

HRID 1088490 reaction equation
[C:1]([OH:12])(=[O:11])/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].C1(C(N)C2CCCCC2)CCCCC1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[H][H]>CO>[C:1]([OH:12])(=[O:11])[CH2:2][CH:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])[CH3:4]

Participants

6

Reactant 4

HCID 634876Binap, (A+-)-HCID 5275520Geranic acidHCID 10774245alpha-CyclohexylcyclohexanemethanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 10402Citronellic acidYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 100 ml autoclave, the inside atmosphere of which had previously been replaced with argon, were placed 0.34 g (2 mmoles) of geranic acid, 20 ml of methanol, and 0.39 g (2 mmoles) of dicyclohexylmethylamine. Then, 5.6 mg (0.007 mmole) of Ru((+)-BINAP)(O2CCH3)2 prepared according to the same manner as in Referential Example 3 except using (+)-BINAP in place of (-)-BINAP was added to the mixture to perform hydrogenation for 12 hours at a hydrogen pressure of 100 kg/cm2 and at a reaction temperature of 25° C. Thereafter, the solvent was distilled off to provide 0.34 g of citronellic acid.

Workup

  1. additionwas added to the mixture
  2. customfor 12 hours
  3. customat a reaction temperature of 25° C
  4. distillationThereafter, the solvent was distilled off

Sources & evidence

ORD record
ord-e5d653c57a04404ca48d684316e0cc6b
Source dataset
uspto-grants-1990_10
Patent number
US04962230

Reaction notes

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