Potassium Hydroxide → 5-[Decyl(dimethyl)silyl]pentanoic acid

HRID 848725Notes

Reaction equation

HRID 848725 reaction equation
C[O:2][C:3](=[O:25])[CH:4](C(OC)=O)[CH2:5][CH2:6][CH2:7][Si:8]([CH3:20])([CH3:19])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH-].[K+]>CO>[CH3:20][Si:8]([CH3:19])([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:25])=[O:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12942701HCID 12942701, compound

Product 1

HCID 129427045-[Decyl(dimethyl)silyl]pentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 6.7 g (18 mmole) of methyl-2-methoxycarbonyl-6,6-dimethyl-6-sila-n-hexadecanoate (from step C) in 50 ml of methanol and 3.0 g (about 48 mmole) of potassium hydroxide (powder) in 50 ml of methanol is refluxed for 45 min. The resulting mixture is then concentrated to a solid. Dilute hydrochloric acid (2N) is then added to the solid (in excess, to acid pH) and the mixture extracted with methylene chloride. The extract is dried, then concentrated to a residue. The residue is heated to 160°-170° under reduced pressure (approx. 15 mm Hg), for 1 hour, then distilled under high vacuum through a jacketed Vigreux column to obtain refined title product of this step (as the main fraction) at 145°-140° at 0.101-0.090 mm Hg.

Workup

  1. temperatureis refluxed for 45 min
  2. concentrationThe resulting mixture is then concentrated to a solid
  3. additionDilute hydrochloric acid (2N) is then added to the solid (in excess, to acid pH)
  4. extractionthe mixture extracted with methylene chloride
  5. customThe extract is dried
  6. concentrationconcentrated to a residue
  7. temperatureThe residue is heated to 160°-170° under reduced pressure (approx. 15 mm Hg), for 1 hour
  8. distillationdistilled under high vacuum through a jacketed Vigreux column

Sources & evidence

ORD record
ord-b28593799bc44db4a2e2d86c5bc9b74e
Source dataset
uspto-grants-1981_10
Patent number
US04297349

Reaction notes

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