Tetrahydrofuran → HCID 15725166, compound

HRID 1085679Notes

Reaction equation

HRID 1085679 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[CH3:12][C:13]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:14]=1[O:15][CH:16]([CH3:20])[C:17](O)=[O:18].[OH-].[Na+]>O>[CH3:12][C:13]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:14]=1[O:15][CH:16]([CH3:20])[CH2:17][OH:18]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 42078482-(2,5-dimethylphenoxy)propanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 15725166HCID 15725166, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred and refluxing mixture of 56 parts of lithium aluminum hydride in 1000 parts of tetrahydrofuran was added dropwise a solution of 359 parts of 2-(2,5-dimethylphenoxy)propanoic acid in 1000 parts of tetrahydrofuran. Upon completion, stirring was continued at reflux temperature for 1.50 hours. The reaction mixture was cooled and decomposed by the successive additions of 55 parts of water, 45 parts of a 15% sodium hydroxide solution and 190 parts of water and the whole was stirred for 30 minutes. The inorganic material was filtered off after acidification with hydrochloric acid solution. The filtrate was dried, filtered and evaporated. The residue was distilled, yielding 73 parts of 2-(2,5-dimethylphenoxy)-1-propanol; bp. 150° C. at 11 mm. pressure (131).

Workup

  1. temperaturerefluxing
  2. stirringUpon completion, stirring
  3. temperatureat reflux temperature for 1.50 hours
  4. temperatureThe reaction mixture was cooled
  5. stirringthe whole was stirred for 30 minutes
  6. filtrationThe inorganic material was filtered off after acidification with hydrochloric acid solution
  7. customThe filtrate was dried
  8. filtrationfiltered
  9. customevaporated
  10. distillationThe residue was distilled

Sources & evidence

ORD record
ord-eb72ea6ada0d49538bab83e450e167c6
Source dataset
uspto-grants-1991_04
Patent number
US05010198

Reaction notes

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