Water → 6-Octyl-1,4-dioxan-2-one

HRID 344985

Reaction equation

HRID 344985 reaction equation
[CH2:1]([OH:12])[CH:2]([OH:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[Na+].Cl[CH2:16][C:17]([O-])=[O:18].[Na+].O>C(OCC)C>[CH2:3]([CH:2]1[O:11][C:17](=[O:18])[CH2:16][O:12][CH2:1]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 791411,2-DecanediolHCID 23665759Sodium chloroacetate

Product 1

HCID 199933606-Octyl-1,4-dioxan-2-oneYield 63%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
55 °C

Procedure

Powdered decane-1,2-diol (0.25 moles) is stirred at room temperature and very well powdered sodium hydroxide (0.25 moles) is added in portions. Gentle heating of the mixture to 55° C. gives a viscous yellow paste. Sodium chloroacetate (0.25 moles) is now added in portions over 10 minutes. The white mobile paste produced is stirred at 70°-60° C. for 1.75 h. After cooling to 20° C., 100 ml of petroleum ether is added followed by water. After separation of phases (aided by acetone) the aqueous phase is run off and acidified to pH 1.5 using 98% sulphuric acid. The oil produced is taken up into 2×375 ml diethyl ether which is then dried and evaporated to leave the title product as a clear oil (63%).

Workup

  1. customgives a viscous yellow paste
  2. customThe white mobile paste produced
  3. temperatureAfter cooling to 20° C.
  4. customAfter separation of phases (aided by acetone) the aqueous phase
  5. customThe oil produced
  6. customis then dried
  7. customevaporated

Sources & evidence

ORD record
ord-1e898af28f254e6ba27446d704bf27c7
Source dataset
uspto-grants-1991_10
Patent number
US05055230

Linked notes

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