Sodium Hydroxide → Decyl glycidyl ether

HRID 2106936Notes

Reaction equation

HRID 2106936 reaction equation
Cl[CH2:2][CH:3]([OH:16])[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[OH-].[Na+]>O>[CH2:6]([O:5][CH2:4][CH:3]1[CH2:2][O:16]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 867122-Propanol, 1-chloro-3-(decyloxy)-

Product 1

HCID 92960Decyl glycidyl etherYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

To the crude 1-chloro-3-decyloxy-2-propanol prepared as described above and cooled to 40° C. was added NaOH (50% aqueous, 176 g, 2.2 mole) and water (44 g). The temperature rose to 50° C., then the mixture was heated to 85° C.-90° C. for three hours. Analysis by GC showed the crude product contained 11% unreacted alcohol and 75% of the expected epoxide. Water (200 ml) was added to dissolve precipitated salt. The aqueous phase was separated (pH 14) and the organic phase washed with 5% NaCl solution to pH 7-8 (2 ×400 ml). The crude product (435 g, 102%) was fractionally distilled at 12 mmHg to yield 286 g of (decyloxy)methyloxirane (67% overall based on epichlorohydrin). GC showed the product was 97% pure.

Workup

  1. customrose to 50° C.
  2. temperaturethe mixture was heated to 85° C.-90° C. for three hours
  3. dissolutionto dissolve
  4. customprecipitated salt
  5. customThe aqueous phase was separated (pH 14)
  6. washthe organic phase washed with 5% NaCl solution to pH 7-8 (2 ×400 ml)
  7. distillationThe crude product (435 g, 102%) was fractionally distilled at 12 mmHg

Sources & evidence

ORD record
ord-19709f5d4b8544fca9d88dabeb562296
Source dataset
uspto-grants-1990_06
Patent number
US04931596

Reaction notes

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