Potassium Hydroxide → (2R,6R)-(+)-2,6,10-trimethylundecan-1-ol

HRID 26776Notes

Reaction equation

HRID 26776 reaction equation
[OH:1][CH2:2][C@H:3]([CH3:16])[CH2:4][C:5](=O)[CH2:6][C@H:7]([CH3:14])[CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12].[OH-].[K+].O.NN>C(O)COCCO>[CH3:16][C@H:3]([CH2:4][CH2:5][CH2:6][C@H:7]([CH3:14])[CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:2][OH:1]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 11042498(2R,6R)-1-hydroxy-2,6,10-trimethylundecan-4-one

Product 1

HCID 10353213(2R,6R)-(+)-2,6,10-trimethylundecan-1-ol

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

A mixture of 3.98 g. (0.0174 mole) of (2R,6R)-1-hydroxy-2,6,10-trimethylundecan-4-one, 108 ml. of diethylene glycol, 25 g. of KOH and 43.5 ml. of hydrazine hydrate was stirred and heated until distillation began. Distillation was then continued until the internal temperature of the reaction mixture reached 195° C. then the mixture was mintained at reflux for 4 hours. After cooling, the resulting mixture was treated with ice and 3 N aqueous HCl and worked-up by ether extraction in the manner of Example 1 giving 2.9 g. of a pale yellow oil. This material was chromatographed on 180 g. of silica gel. Elution with 4:1 parts by volume hexane-ether yielded (2R,6R)-(+)-2,6,10-trimethylundecan-1-ol which was evaporatively distilled affording 2.22 g. of a colorless oil, b.p. 90°-105° C. (bath temperature) (0.2 mm Hg.); [α]25D+ 9.44° (c 2.04, hexane).

Workup

  1. additionA mixture of 3.98 g
  2. temperatureheated until distillation
  3. distillationDistillation
  4. customreached 195° C.
  5. temperatureat reflux for 4 hours
  6. temperatureAfter cooling
  7. additionthe resulting mixture was treated with ice and 3 N aqueous HCl
  8. extractionworked-up by ether extraction in the manner of Example 1 giving 2.9 g
  9. customThis material was chromatographed on 180 g
  10. washElution with 4:1 parts by volume hexane-ether

Sources & evidence

ORD record
ord-3ebd2558f3104815a5ab360475dfe70b
Source dataset
uspto-grants-1979_04
Patent number
US04151205

Reaction notes

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