Tetrahydrofuran → HCID 54261585, compound

HRID 1111793Notes

Reaction equation

HRID 1111793 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:8]=2[C:9](O)=[O:10])=[CH:4][CH:3]=1.O1CCCC1.[OH-].[Na+]>C1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:8]=2[CH2:9][OH:10])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 137380552-(4-Methylphenoxy)-5-methyl-benzoic acid

Product 1

HCID 54261585HCID 54261585, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 121 g. of 2-(4-methyl-phenoxy)-5-methyl-benzoic acid in 600 ml. of tetrahydrofuran is slowly added dropwise, with cooling in an icebath, to 420 ml. of a 70% solution of sodium dihydro-bis(1-methoxyethoxy)aluminate in benzene and stirred for an additional hour at room temperature. To the obtained clear solution, 800 ml. of 20% aqueous sodium hydroxide solution are carefully added dropwise. Then, the organic phase is separated. The aqueous phase is extracted three additional times with ether. The organic extracts are washed with saturated sodium chloride solution and the latter dried over sodium sulfate. After evaporation of the ether, there is obtained 2-(4-methylphenoxy)-5-methyl-benzyl alcohol as an oil.

Workup

  1. temperaturewith cooling in an icebath, to 420 ml
  2. customThen, the organic phase is separated
  3. extractionThe aqueous phase is extracted three additional times with ether
  4. washThe organic extracts are washed with saturated sodium chloride solution
  5. dry with materialthe latter dried over sodium sulfate
  6. customAfter evaporation of the ether

Sources & evidence

ORD record
ord-64b661680d82492fb063131260318779
Source dataset
uspto-grants-1978_10
Patent number
US04118572

Reaction notes

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