Water → HCID 178442839, compound

HRID 1164550Notes

Reaction equation

HRID 1164550 reaction equation
[CH3:1][CH:2]([C:15]1([O:21][CH2:20]1)[C:16]([O:18]C)=[S:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[O-]CC.[Na+].O>C(O)C>[CH3:1][CH:2]([C:15]1([O:21][CH2:20]1)[C:16]([OH:18])=[S:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 86736905HCID 86736905, compound

Product 1

HCID 178442839HCID 178442839, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.15 g (0.01 mole) of methyl 2-tetradecylthioglycidate in 50 ml of absolute ethanol is added dropwise to a cooled (0°-5° C.) solution of sodium ethoxide (0.25 g sodium in 12 ml absolute ethanol). The mixture is stirred for 15 minutes while maintaining the temperature below 20° C. and 0.19 g of water is added. Stirring is continued overnight (about 15 hours) at room temperature. The resulting suspension is filtered and the precipitate washed with ether, dried and then stirred for several hours in dilute HCl. The acidic suspension is extracted with ether and the ether layer dried (Na2SO4) and evaporated in vacuo giving the product, 2-tetradecylthioglycidic acid, in good yield.

Workup

  1. additionis added
  2. stirringStirring
  3. waitis continued overnight
  4. custom(about 15 hours)
  5. customat room temperature
  6. filtrationThe resulting suspension is filtered
  7. washthe precipitate washed with ether
  8. customdried
  9. stirringstirred for several hours in dilute HCl
  10. extractionThe acidic suspension is extracted with ether
  11. dry with materialthe ether layer dried (Na2SO4)
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-a65201084e5e490580de90558e2b55eb
Source dataset
uspto-grants-1983_01
Patent number
US04370343

Reaction notes

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