Benzoic Acid → 3-Ethoxy-4-oxahexyl benzoate

HRID 1709645Notes

Reaction equation

HRID 1709645 reaction equation
[Na].[C:2]([OH:10])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:11]([O:13][CH:14]([O:18][CH2:19][CH3:20])[CH2:15][CH2:16]Cl)[CH3:12].O>CN(C)C=O>[C:2]([O:10][CH2:16][CH2:15][CH:14]([O:18][CH2:19][CH3:20])[O:13][CH2:11][CH3:12])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 962WaterHCID 962173-Chloro-1,1-diethoxypropaneHCID 5360545Sodium

Product 1

HCID 148558813-Ethoxy-4-oxahexyl benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 50.0 grams (0.347 mole) of the sodium salt of benzoic acid and 53.0 grams (0.320 mole) of 3-ethoxy-4-oxahexyl chloride in 500 ml of dimethylformamide was heated at reflux for three hours. The reaction mixture was cooled to ambient temperature, and 500 ml of water was added. The mixture was extracted with two 700 ml portions of diethyl ether. The combined extracts were dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure yielding 57.5 grams of 3-ethoxy-4-oxahexyl benzoate. The nmr spectrum was consistent with the proposed structure. Further extraction of the aqueous layer with diethyl ether yielded an additional 34.7 grams of the benzoate.

Workup

  1. temperatureat reflux for three hours
  2. extractionThe mixture was extracted with two 700 ml portions of diethyl ether
  3. dry with materialThe combined extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f30eb03dffc947a4b6dca454d72d8c82
Source dataset
uspto-grants-1990_08
Patent number
US04950666

Reaction notes

Loading…