Acetone → 1,2-Decanediol

HRID 1076941

Reaction equation

HRID 1076941 reaction equation
CC(C)=[O:3].C1OC1CCCCCCC.[CH2:15]1[O:25][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>>[CH2:15]([OH:25])[CH:16]([OH:3])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 3

HCID 180AcetoneHCID 169931,2-EpoxydecaneHCID 5511812-Heptyloxirane

Product 1

HCID 791411,2-Decanediol

Procedure

A homogeneous clear solution is prepared by adding 3 moles of acetone to 1 mole of a mixture of 1-nonene oxide and 1-decene oxide at room temperature. After 50 grams of 5% aqueous sulfuric acid to the solution, the acetone is evaporated off and the resulting solution is neutralized by adding an aqueous sodium hydroxide. The neutralized solution is extracted with pet ether and the extract dried over anhydrous magnesium sulfate. The pet ether is stripped off and a mixture of 1,2-nonanediol and 1,2-decanediol is obtained by distilling under vacuo.

Workup

  1. customA homogeneous clear solution is prepared
  2. customAfter 50 grams of 5% aqueous sulfuric acid to the solution, the acetone is evaporated off
  3. additionby adding an aqueous sodium hydroxide
  4. extractionThe neutralized solution is extracted with pet ether
  5. dry with materialthe extract dried over anhydrous magnesium sulfate
  6. additiona mixture of 1,2-nonanediol

Sources & evidence

ORD record
ord-695aadb6f1de4cf78c0370d7d2733131
Source dataset
uspto-grants-1976_05
Patent number
US03959185

Linked notes

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