Sulfuric Acid → Ethyl 3-hydroxyoctanoate

HRID 1060259Notes

Reaction equation

HRID 1060259 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:8](=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.[Zn]>[OH:14][CH:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 6184HexanalHCID 7748Ethyl bromoacetate

Product 1

HCID 110975Ethyl 3-hydroxyoctanoate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1140TolueneSolvent

Conditions

Temperature
83 °C

Procedure

7.64 g (0.117 mol) of zinc pretreated as described in Reference Example 1 were suspended in 50 ml of toluene, the mixture was heated to 83° C., the heat source was subsequently removed and a mixture of 11.4 ml (0.103 mol) of ethyl bromoacetate and 11.23 ml (0.0935 mol) of hexanal was added dropwise over a period of 30 minutes. After a brief induction phase, rigorous foaming and heating of the reaction mixture to 110° C. was observed. After all the mixture had been added, the resulting suspension was cooled to 8° C. by means of an ice/water mixture, after which 15 ml of 50% strength sulfuric acid was added dropwise at such a rate that the temperature of the suspension did not exceed 35° C. After phase separation, the organic phase was washed twice with 15 ml of water and dried over sodium sulfate. After filtration and removal of all volatile constituents on a rotary evaporator at 50° C./5 torr, the residue obtained was distilled in an oil pump vacuum at 2.5 torr. The fraction comprising ethyl 3-hydroxyoctanoate went over at 88-93° C. Yield: 12.25 g (70%).

Workup

  1. customthe heat source was subsequently removed
  2. additionwas added dropwise over a period of 30 minutes
  3. temperatureAfter a brief induction phase, rigorous foaming and heating of the reaction mixture to 110° C.
  4. additionAfter all the mixture had been added
  5. customdid not exceed 35° C
  6. customAfter phase separation
  7. washthe organic phase was washed twice with 15 ml of water
  8. dry with materialdried over sodium sulfate
  9. filtrationAfter filtration and removal of all volatile constituents
  10. customon a rotary evaporator at 50° C./5 torr
  11. customthe residue obtained
  12. distillationwas distilled in an oil pump vacuum at 2.5 torr
  13. customwent over at 88-93° C

Sources & evidence

ORD record
ord-97bbfb53ee5a4f98a179809da3cb6024
Source dataset
uspto-grants-2003_02
Patent number
US06521771B2

Reaction notes

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