1-Butanol → 2-Hydroxydecyl-butyl ether

HRID 267606

Reaction equation

HRID 267606 reaction equation
[Na].[CH2:2]([OH:6])[CH2:3][CH2:4][CH3:5].[O:7]1[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:8]1>>[OH:7][CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:8][O:6][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 169931,2-EpoxydecaneHCID 5360545Sodium2×

Product 1

HCID 104664152-Hydroxydecyl-butyl etherYield 87%

Conditions

Temperature
100 °C

Procedure

0.46 gm (0.02 gm-atom) of sodium were added to 185 gm (2.5 mols) of n-butanol. After dissolution of the sodium, the temperature was raised to 100°C, and an amount of 78.2 gm (0.5 mol) of 1,2-epoxy decane was added in drops within 30 minutes while stirring. The reaction mixture was maintained at 100°C for 4 hours. Then the excess alcohol was distilled, and by subsequent vacuum distillation at 100° to 120°C and 0.06 Torr . the 2-hydroxy-decyl-n-butyl ether was separated from the higher boiling by-product. In this manner the intermediate product 2-hydroxydecyl-n-butyl ether (refractive index nD20 = 1.4392) was obtained in a yield of 87%.

Workup

  1. temperatureThe reaction mixture was maintained at 100°C for 4 hours
  2. distillationThen the excess alcohol was distilled
  3. distillationby subsequent vacuum distillation at 100° to 120°C
  4. customthe 2-hydroxy-decyl-n-butyl ether was separated from the higher boiling by-product

Sources & evidence

ORD record
ord-69818f78eb614490b23a55445d05aee6
Source dataset
uspto-grants-1976_03
Patent number
US03943178

Linked notes

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