Potassium Hydroxide → 1-Dodecanol, 3,7,11-trimethyl-, (R*,R*)-

HRID 1659825Notes

Reaction equation

HRID 1659825 reaction equation
Cl[CH2:2][CH2:3][C@H:4]([CH3:16])[CH2:5][CH2:6][CH2:7][C@H:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13].C([O-])(=[O:19])C.[K+].[OH-].[K+]>C(Cl)(Cl)Cl.CN(C)C=O>[CH3:16][C@H:4]([CH2:5][CH2:6][CH2:7][C@H:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:3][CH2:2][OH:19]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 517044Potassium AcetateHCID 13191849HCID 13191849, compound

Product 1

HCID 1590641-Dodecanol, 3,7,11-trimethyl-, (R*,R*)-Yield 94%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

For the verification of the optical purity the compound obtained is hydrogenated on pre-hydrogenated platinum dioxide to (3R,7R)-1-chloro-3,7,11-trimethyldodecane; boiling point at 0.07 mm; 90°; αD =-1.2° (4.08% in CHCl3), which is converted by heating with dry potassium acetate in dimethylformamide (4 hours at 170°). This ester is purified by adsorption on silicagel (elution agent: n-hexane/ether 4+1), then further reacted to (3R,7R)-3,7,11-trimethyl-1-dodecanol by stirring with 4-N aqurous caustic potash (30 min. at room temperature). The mixture is extracted, washed neutral, dried, concentrated, distilled in the bulb-tube (115°, 0.20 Torr) and there is obtained (3R,7R)-3,7,11-trimethyl-1-dodecanol in 94% yield (based on (3R,7R)-1-chloro-3,7,11-trimethyldodecane employed). The product has an optical rotation value of [α]D20 =+3.7° (4.14% in n-octane) and is accordingly identical with authentic material.

Workup

  1. customFor the verification of the optical purity the compound obtained
  2. custom90°
  3. customThis ester is purified by adsorption on silicagel (elution agent: n-hexane/ether 4+1)
  4. customfurther reacted to (3R,7R)-3,7,11-trimethyl-1-dodecanol
  5. extractionThe mixture is extracted
  6. washwashed neutral
  7. customdried
  8. concentrationconcentrated
  9. distillationdistilled in the bulb-tube (115°, 0.20 Torr)

Sources & evidence

ORD record
ord-5f90aaec506c4d6ab56ea40175b40aae
Source dataset
uspto-grants-1981_12
Patent number
US04305876

Reaction notes

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