Hydrochloric Acid → 4-Phenoxy-2-butanol

HRID 1381297Notes

Reaction equation

HRID 1381297 reaction equation
[O:1]([CH2:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][Mg]I.Cl>C(OCC)C>[O:1]([CH2:8][CH2:9][CH:10]([OH:11])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 109864123-PhenoxypropanalHCID 178418373HCID 178418373, compound

Product 1

HCID 113787034-Phenoxy-2-butanolYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

24.9 g of methyl iodide was reacted with 7.26 g of magnesium in 150 ml of anhydrous diethyl ether to obtain methylmagnesium iodide by Grignard reaction. To a solution consisting of 20 g of 3-phenoxypropionaldehyde and 200 ml of anhydrous diethyl ether was added dropwise the methylmagnesium while maintaining a temperature of not more than 20° C. To the reaction solution was added 25 ml of concentrated hydrochloric acid and the solution was separated into two phases, which phases were then separated from each other. The ether layer was washed with an aqueous sodium bicarbonate solution, washed with water, dried with anhydrous sodium sulfate and then condensed under reduced pressure to obtain 15.0 g of 4-phenoxy-2-butanol having a boiling point of 61° C. to 62° C. at 3 mmHg in a yield of 67%.

Workup

  1. customby Grignard reaction
  2. temperaturewhile maintaining a temperature of not more than 20° C
  3. customthe solution was separated into two phases, which phases
  4. customwere then separated from each other
  5. washThe ether layer was washed with an aqueous sodium bicarbonate solution
  6. washwashed with water
  7. dry with materialdried with anhydrous sodium sulfate
  8. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-ffd6704236304050958e67ead0774441
Source dataset
uspto-grants-1986_04
Patent number
US04585869

Reaction notes

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