Solketal → Bis[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]isophthalate

HRID 436392

Reaction equation

HRID 436392 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[C:10]([O:22][CH3:23])(=[O:21])[C:11]1[CH:20]=[CH:19][CH:18]=[C:13]([C:14]([O:16]C)=O)[CH:12]=1.[CH3:24][O-:25].[Na+].[H][H]>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][O:8][C:14](=[O:16])[C:13]2[CH:18]=[CH:19][CH:20]=[C:11]([C:10]([O:22][CH2:23][CH:24]3[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:25]3)=[O:21])[CH:12]=2)[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 7528SolketalHCID 15088Dimethyl isophthalateHCID 10942334Sodium MethoxideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 53701685Bis[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]isophthalate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

Into a five liter capacity, four-necked flask equipped with a thermometer, stirrer, nitrogen inlet and a 10-inch helix packed column were placed 1322 grams (10 moles) of 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane (Comonomer A herein), 971 grams (5 moles) of dimethyl isophthalate, 1700 grams of dry toluene and 7 grams of sodium methoxide. The reaction mixture was heated to reflux. During 5 hours, a binary mixture (927 grams) of toluene-methanol was collected at a head temperature of 95°-106° C. by maintaining a flask temperature of 137°-145° C. After cooling to 25° C., 500 ml. of dichloromethane was dissolved in the reaction mixture. The resulting mixture was washed with four 1000 ml. portions of 5 per cent aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated to give a crude amber-colored oil. Distillation of the oil afforded 999.5 grams (51 per cent yield) of substantially pure white product having a boiling point of 205°-212° C. (at 0.50-0.60 mm. pressure). Analysis of the product showed carbon and hydrogen contents of 60.74 and 6.83 weight per cent, respectively. The calculated carbon and hydrogen contents (basis, C20H26O8) are 60.91 and 6.59 respectively.

Workup

  1. customInto a five liter capacity, four-necked flask equipped with a thermometer, stirrer, nitrogen inlet
  2. temperatureThe reaction mixture was heated to reflux
  3. customa binary mixture (927 grams) of toluene-methanol was collected at a head temperature of 95°-106° C.
  4. temperatureby maintaining a flask temperature of 137°-145° C
  5. dissolutionof dichloromethane was dissolved in the reaction mixture
  6. washThe resulting mixture was washed with four 1000 ml
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto give a crude amber-colored oil
  11. distillationDistillation of the oil
  12. customafforded
  13. custom999.5 grams (51 per cent yield) of substantially pure white product

Sources & evidence

ORD record
ord-eefd3985dafb4d56ae1e5f3f08074fa0
Source dataset
uspto-grants-1977_02
Patent number
US04009129

Linked notes

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