Benzoic Acid → HCID 67433308, compound

HRID 1709714Notes

Reaction equation

HRID 1709714 reaction equation
[CH3:1][O:2][CH:3]([CH2:5][O:6][CH:7]([CH2:9][O:10][CH:11]([CH2:13][OH:14])[CH3:12])[CH3:8])[CH3:4].[C:15](O)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(=O)([O-])[O-].[Zn+2].C1(C)C=CC=CC=1>[C:15]([O:14][CH2:13][CH:11]([CH3:12])[O:10][CH2:9][CH:7]([CH3:8])[O:6][CH2:5][CH:3]([O:2][CH3:1])[CH3:4])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 243Benzoic AcidHCID 250541-Propanol, 2-(2-(2-methoxypropoxy)propoxy)-

Product 1

HCID 67433308HCID 67433308, compoundYield 110.5%

Reagents, catalysts & solvents 2

HCID 19005Zinc CarbonateCatalystHCID 1140TolueneSolvent

Procedure

Tripropylene glycol monomethyl ether (841.6 grams; 3.39 mol), benzoic acid (501.7 grams; 3.46 mol), zinc carbonate 13.5 grams) and toluene (100 ml) were placed into a two liter, three-necked round bottom flask equipped with stirrer, 10" Vigreux column, Dean Stark trap, condenser, heating mantle and thermometer. The reaction temperature was 173° .C at the beginning of the reaction and 235° C. after six hours and 48 minutes. During that time, water (70 ml) was removed. The reaction was continued the next day at 214° C. for an additional three hours and 45 minutes removing additional water (35 ml). Toluene was removed at 65° C. @ 45 mm Hg. The product was washed first with sodium carbonate (170 ml; 15%) at 95°-100° C. for 30 minutes, then with sodium carbonate (22 ml; 15%) and sodium hypochlorite (50 ml), then with sodium carbonate (22 ml; 15%) and sodium hypochlorite (25 ml) with water (300 ml) and finally a second time with water (300 ml). It was dried at 135° C. and filtered to give the desired product (1162.9 grams; 93.6% yield). The product assayed with the following properties:

Workup

  1. customequipped with stirrer
  2. temperature10" Vigreux column, Dean Stark trap, condenser, heating mantle
  3. customwas 173°
  4. customat the beginning of the reaction and 235° C. after six hours
  5. custom48 minutes
  6. customDuring that time, water (70 ml) was removed
  7. customat 214° C.
  8. customfor an additional three hours
  9. custom45 minutes removing additional water (35 ml)
  10. customToluene was removed at 65° C. @ 45 mm Hg
  11. washThe product was washed first with sodium carbonate (170 ml; 15%) at 95°-100° C. for 30 minutes
  12. customIt was dried at 135° C.
  13. filtrationfiltered

Sources & evidence

ORD record
ord-7eec73ed658a47418637831d1a8b4b7f
Source dataset
uspto-grants-1990_08
Patent number
US04950702

Reaction notes

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