Hydrochloric Acid → ethyl 3-hydroxydecanoate

HRID 404608Notes

Reaction equation

HRID 404608 reaction equation
Cl.[CH:2](=[O:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]CC.[CH3:13][CH2:14][O:15][C:16]([CH2:18]Br)=[O:17].S(=O)(=O)(O)O>[Zn].C1C=CC=CC=1>[CH2:14]([O:15][C:16](=[O:17])[CH2:18][CH:2]([OH:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 7748Ethyl bromoacetateHCID 8175Decanal

Product 1

HCID 11031260ethyl 3-hydroxydecanoateYield 93%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent

Procedure

7.8 g of zinc activated by a hydrochloric acid and 25 ml of benzene were placed in a circulation device incorporating the Dean and Stark device. The solution was circulated while heated. To the resultant solution, a mixed solution of 15.6 g (100 mmol) of decanal and 18.4 g (110 mmol) of bromoacetic acid ethyl was dropped. After six hours, the solution was cooled to room temperature. A 50% (w/w) sulfuric acid was added to divide the solvent, and the organic layer was separated. The organic layer was dried with magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=2/8). As a result, a 3-hydroxydecanoic acid ethyl ester was obtained.

Workup

  1. temperaturewhile heated
  2. customthe organic layer was separated
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=2/8)

Sources & evidence

ORD record
ord-dba4f4097e29453ca79d89033705a12d
Source dataset
uspto-grants-2014_06
Patent number
US08748617B2

Reaction notes

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