Benzoic Acid → Ethanol, 2-(2-phenoxyethoxy)-, 1-benzoate

HRID 1400785Notes

Reaction equation

HRID 1400785 reaction equation
[C:1]1([O:7][CH:8]([CH2:10][O:11][CH:12]([CH2:14][OH:15])C)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](O)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCCCCCC>S(=O)(=O)(O)O.O>[C:16]([O:15][CH2:14][CH2:12][O:11][CH2:10][CH2:8][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 243Benzoic AcidHCID 8900Heptane2×HCID 668245772-(2-Phenoxypropoxy)propan-1-ol

Product 1

HCID 105772Ethanol, 2-(2-phenoxyethoxy)-, 1-benzoate

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

In a 2-L one-neck flask equipped with a magnetic stirrer, a heating mantle, and a Dean-Stark trap connected to a nitrogen purged condenser were placed 517.5 g dipropylene glycol phenyl ether technical grade containing a total hydroxyl content of 3.0 moles, 363.3 g (2.97 mole) benzoic acid, 300 ml heptane, and 20 drops concentrated sulfuric acid. The flask was heated to 115° C. to establish a constant heptane reflux through the trap where the water of esterification was collected. The reaction was allowed to continue for a total of 48 hours, at which point the theoretical amount of water was collected. The reaction mixture was cooled to 25° C. and then filtered through a small bed of activated basic alumina to neutralize the catalyst. The filtrate was placed in a boiling flask and the heptane removed at low pressure in a Büchi rotary evaporator. The residue was flash distilled under vacuum to isolate the diethylene glycol phenyl ether benzoate boiling at 165° C. @ 0.1 mmHg. The boiling point at reduced pressure was corrected to the normal boiling by means of a computer program that fits vapor pressure data to an Antoine equation of the form log P=A−B/(T+C). The normal boiling point was calculated at approximately 440° C. A sample of the product was then tested as specified by EPA Method 24 and found to contain only 0.7 percent volatiles.

Workup

  1. customIn a 2-L one-neck flask equipped with a magnetic stirrer
  2. customa heating mantle, and a Dean-Stark trap connected to a nitrogen purged condenser
  3. customwas collected
  4. customto continue for a total of 48 hours, at which point
  5. customwas collected
  6. temperatureThe reaction mixture was cooled to 25° C.
  7. filtrationfiltered through a small bed of activated basic alumina
  8. customThe filtrate was placed in a boiling flask
  9. customthe heptane removed at low pressure in a Büchi rotary evaporator
  10. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-62af93b48dc143e798de1630858565d5
Source dataset
uspto-grants-2014_12
Patent number
US08906991B2

Reaction notes

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