Ethylene Glycol → HCID 12596328, compound

HRID 2414714Notes

Reaction equation

HRID 2414714 reaction equation
[C:1]1(=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9](=[O:17])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:19](O)[CH2:20][OH:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[O:18]1[C:1]2([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[O:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 11345773HCID 11345773, compound

Product 1

HCID 12596328HCID 12596328, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 44.0 g (175 mmol) of 1,9-cyclohexadecanedione in 125 ml of toluene is added 13.1 g (210 mmol) of ethylene glycol and 500 mg (2.5 mmol) of p-toluenesulphonic acid. The mixture is then heated with a water separator until visible amounts of water are no longer eliminated. Washing with sat. NaHCO3 solution is then carried out, the phases are separated, the organic phase is dried over Na2SO4, filtration is carried out, and the solvent is removed on a rotary evaporator. This gives 57.7 g of a solid comprising 3 components having the following GC content: 1,9-cyclohexadecanedione (33.7%); 1,4-dioxaspiro-[4.15]-eicosan-13-one (52.5%); 1,4,14,17-tetraoxadispiro-[4.7.4.7]-tetracosane (13.2%).

Workup

  1. washWashing with sat. NaHCO3 solution
  2. customthe phases are separated
  3. dry with materialthe organic phase is dried over Na2SO4, filtration
  4. customthe solvent is removed on a rotary evaporator

Sources & evidence

ORD record
ord-0c0cb7922e144bc7a0eaa50f0b0636f8
Source dataset
uspto-grants-2004_11
Patent number
US06815413B2

Reaction notes

Loading…