3-Chloro-1,1-diethoxypropane → 3-Ethoxy-4-oxahexyl benzoate

HRID 1090467Notes

Reaction equation

HRID 1090467 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].Cl[CH2:12][CH2:13][CH:14]([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17]>CN(C)C=O>[C:1]([O:9][CH2:12][CH2:13][CH:14]([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962173-Chloro-1,1-diethoxypropaneHCID 517055Sodium Benzoate

Product 1

HCID 148558813-Ethoxy-4-oxahexyl benzoateYield 80.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5.0 grams (0.034 mole) of sodium benzoate in 100 ml of dimethylformamide was added 5.2 grams (0.031 mole) of 3-chloro-1,1-diethoxypropane. Upon completion of addition, the reaction mixture was warmed to reflux where it stirred for four hours. After this time the reaction mixture was cooled to ambient temperature and was filtered to remove a solid. The filtrate was diluted with water, and the mixture was extracted with diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The nmr spectrum indicated the presence of solvents. The oil was redissolved in diethyl ether and washed with water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was evacuated under high vacuum yielding 6.3 grams of 3-ethoxy-4-oxahexyl benzoate. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. temperaturethe reaction mixture was warmed
  3. temperatureto reflux where it
  4. filtrationwas filtered
  5. customto remove a solid
  6. additionThe filtrate was diluted with water
  7. extractionthe mixture was extracted with diethyl ether
  8. dry with materialThe combined extracts were dried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  11. dissolutionThe oil was redissolved in diethyl ether
  12. washwashed with water
  13. dry with materialThe organic layer was dried with magnesium sulfate
  14. filtrationfiltered
  15. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  16. customThe oil was evacuated under high vacuum

Sources & evidence

ORD record
ord-e62c2e1446a040f496a7b9cf09f3f35d
Source dataset
uspto-grants-1992_01
Patent number
US05081287

Reaction notes

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