Hydrochloric Acid → 4-Phenoxy-2-butanol

HRID 484830Notes

Reaction equation

HRID 484830 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. The reaction solution was added with 25 ml of concentrated hydrochloric acid, and then the diethyl ether layer was separated from an aqueous layer. The ether layer was washed with an aqueous sodium bicarbonate solution, washed with water, dried over 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 diethyl ether layer was separated from an aqueous layer
  4. washThe ether layer was washed with an aqueous sodium bicarbonate solution
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-327f8647fe954b34bbd87b90997492fc
Source dataset
uspto-grants-1985_08
Patent number
US04533731

Reaction notes

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