Ethylene Glycol → 2-hydroxyethyl dodecylcarbamate

HRID 986094Notes

Reaction equation

HRID 986094 reaction equation
[CH2:1]([N:13]=[C:14]=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:16]([OH:19])[CH2:17][OH:18]>O1CCCC1>[CH2:1]([NH:13][C:14](=[O:15])[O:18][CH2:17][CH2:16][OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 77873Dodecane, 1-isocyanato-

Product 1

HCID 2391962-hydroxyethyl dodecylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.2 ml dodecyl isocyanate and 2.4 ml of ethylene glycol are combined in tetrahydrofuran at room temperature and stirred overnight at room temperature. The resultant material is evaporated under reduced pressure (<30° C.), dried in vacuo, and purified by chromatography on a silica gel column using ethyl acetate as elutant. Fractions 74-94 are combined (Rf 0.75 TLC Silica gel ethyl acetate iodine detection), evaporated under reduced pressure (<30° C.) and dried in vacuo to yield 546 mg of title product.

Workup

  1. customThe resultant material is evaporated under reduced pressure (<30° C.)
  2. customdried in vacuo
  3. custompurified by chromatography on a silica gel column
  4. customevaporated under reduced pressure (<30° C.)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-45f10da449324afeae1723a1f85d2dd8
Source dataset
uspto-grants-1987_12
Patent number
US04710580

Reaction notes

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