Water → HCID 21317597, compound

HRID 263003Notes

Reaction equation

HRID 263003 reaction equation
Cl[CH2:2][CH2:3][S:4]([CH:7]([CH2:19][CH2:20][CH2:21][CH:22]([O:28]C(=O)C)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])(=[O:6])=[O:5].[OH-].[Na+].O>O1CCCC1>[CH:3]([S:4]([CH:7]([CH2:19][CH2:20][CH2:21][CH:22]([OH:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])(=[O:6])=[O:5])=[CH2:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21317539HCID 21317539, compound

Product 1

HCID 21317597HCID 21317597, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of ethyl 8-(2-chloroethylsulfonyl)-12-acetoxyheptadecanoate (43.5 g., 0.09 mole), sodium hydroxide (14.4 g., 0.36 mole), water (150 ml.) and tetrahydrofuran (600 ml.) is stirred at 25° C. for 24 hours. Most of the tetrahydrofuran is removed by evaporation in vacuo keeping the temperature of the evaporating solution at 30° C. or below. The residue is diluted with water (300 ml.) and extracted with ether. The aqueous solution is acidified with dilute hydrochloric acid. The oily product is taken up in ether, washed with water and dried over sodium sulfate. The ether is evaporated to leave the product as a yellowish, very viscous oil. Purification is effected by column chromatography on silica gel with benzene-dioxane as eluting solvent mixture. The title compound is obtained as a colorless viscous oil.

Workup

  1. customMost of the tetrahydrofuran is removed by evaporation in vacuo
  2. customat 30° C. or below
  3. additionThe residue is diluted with water (300 ml.)
  4. extractionextracted with ether
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customThe ether is evaporated
  8. customto leave the product as a yellowish, very viscous oil
  9. customPurification
  10. washas eluting solvent mixture

Sources & evidence

ORD record
ord-cb529b716cee4d168423a7381c29d3bf
Source dataset
uspto-grants-1979_05
Patent number
US04155908

Reaction notes

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