Nerol → Beta-citronellol, (S)-

HRID 1033865

Reaction equation

HRID 1033865 reaction equation
[OH:1][CH2:2]/[CH:3]=[C:4](/[CH3:11])\[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9].[H][H]>C1C=CC=CC=1>[CH3:9][C:8](=[CH:7][CH2:6][CH2:5][C@@H:4]([CH2:3][CH2:2][OH:1])[CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 643820NerolHCID 178418361HCID 178418361, compound

Product 1

HCID 7793Beta-citronellol, (S)-Yield 93.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a 100 ml stainless steel-made autoclave whose atmosphere had been displaced with nitrogen were charged 1.54 g (10 mmole) of nerol, 0.0837 g (0.1 mmole) of Rh(COD)((+)-cBINAP)Cl obtained in Example 4, and 10 ml of benzene, and hydrogenation reaction was carried out at room temperature and at a hydrogen pressure of 30 kg/cm2 for 17 hours. There was obtained 1.46 g of (S)-(-)-citronellol at a conversion of 99% and a selectivity of 99%. From the results of optical rotation [α]25D =-3.65° (c=10.1, chloroform), the optical yield was found to be 70%ee.

Workup

  1. additionwere charged

Sources & evidence

ORD record
ord-40c1ffd65a72440ca4c4af287452b7d2
Source dataset
uspto-grants-1994_05
Patent number
US05312939

Linked notes

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