Geraniol → 3,7-Dimethyl-1-octanol

HRID 1014772Notes

Reaction equation

HRID 1014772 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6]/[C:7](=[CH:9]/[CH2:10][OH:11])/[CH3:8])[CH3:3]>C(Cl)Cl>[CH3:8][CH:7]([CH2:6][CH2:5][CH2:4][CH:2]([CH3:3])[CH3:1])[CH2:9][CH2:10][OH:11]

Participants

3

Reactant 1

HCID 637566Geraniol

Product 1

HCID 77923,7-Dimethyl-1-octanolYield 102.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the general procedure, a solution of geraniol (52 μL, 0.29 mmol) and rac-32 (9.0 mg, 0.0057 mmol, 2.0 mol %) in CH2Cl2 (3 mL) was pressurized with H2 to 62 bar and stirred for 24 h. Filtration of the reaction mixture and evaporation of the solvent gave 44 as a clear liquid (47 mg, 98%). 1H NMR30 (300 MHz, CDCl3): δ 3.68 (m, 2H), 1.61-1.17 (m, 10H), 0.90 (s, 9H); 13C NMR (75.5 MHz, CDCl3): δ 61.4, 30.1, 39.4, 37.5, 29.7, 28.1, 24.8, 22.8, 22.7, 19.8.

Workup

  1. filtrationFiltration of the reaction mixture and evaporation of the solvent

Sources & evidence

ORD record
ord-f2acf13745e24c7b98a3bff6072d2127
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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