Sodium Hydroxide → HCID 21317551, compound

HRID 328768Notes

Reaction equation

HRID 328768 reaction equation
[CH3:1][S:2][CH:3]([CH2:13][CH2:14][CH2:15][CH:16]([OH:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].[OH-].[Na+].I([O-])(=O)(=O)=[O:26].[Na+]>O>[CH3:1][S:2]([CH:3]([CH2:13][CH2:14][CH2:15][CH:16]([OH:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:26]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21317582HCID 21317582, compoundHCID 23667635Sodium periodate

Product 1

HCID 21317551HCID 21317551, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8-Methylthio-12-hydroxyheptadecanoic acid (Ex. 1) (6.7 g., 0.0202 mole) is dissolved in a solution of sodium hydroxide (1.0 g., 0.025 mole) in water (80 ml.). Sodium metaperiodate (4.7 g., 0.022 mole) is added and the resulting mixture is stirred at room temperature overnight (17 hours). The solids present are then filtered off and the filtrate is acidified with dilute hydrochloric acid to liberate the oily acid product. The oil is taken up in ether, washed with water and dried over sodium sulfate. The ether is evaporated in vacuo to leave the crude 8-methylsulfinyl-12-hydroxy-heptadecanoic acid as a viscous yellowish oil weighing 5.8 g. Purification is effected by chromatography on a column containing 125 g. of silica gel using 4% methanol in chloroform as eluant. There is obtained 2.2 g. of pure 8-methylsulfinyl-12-hydroxyheptadecanoic acid, a colorless viscous oil with Rf 0.14 on silica gel thin layer chromatograms with chloroform-methanol-acetic acid 96:3:1 as eluant; pmr (CDCl3) δ0.90 (3H, t); 2.50 (3H, s CH3SO); 3.64 (1H, m HCO).

Workup

  1. filtrationThe solids present are then filtered off
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. customThe ether is evaporated in vacuo

Sources & evidence

ORD record
ord-76dcc4595e624a1f8b659f6d4400cb2a
Source dataset
uspto-grants-1977_04
Patent number
US04018802

Reaction notes

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