Tetrahydrofuran → (2-Methoxy-4-propylphenyl)methanol

HRID 602832Notes

Reaction equation

HRID 602832 reaction equation
COCCO[AlH2-]O[CH2:8][CH2:9][O:10][CH3:11].[Na+].[C:13]1(C)[CH:18]=CC=[CH:15][CH:14]=1.[O:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>CO>[CH3:11][O:10][C:9]1[CH:8]=[C:18]([CH2:13][CH2:14][CH3:15])[CH:24]=[CH:23][C:22]=1[CH2:21][OH:20]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724148Sodium potassium tartrate tetrahydrateHCID 131728749Red-Al toluene

Product 1

HCID 59582157(2-Methoxy-4-propylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

Red-Al/toluene solution (66.5% content, 2.05 g) was slowly added to a tetrahydrofuran (3 mL) solution of the compound (1.00 g) prepared in Example 43 at an internal temperature of 5° C., followed by stirring at an internal temperature of about 35° C. for about 2.5 hours. Methanol (0.5 mL) was added to the reaction solution at an internal temperature of 9° C. to stop the reaction. The reaction solution was poured into a 50% aqueous potassium sodium tartrate tetrahydrate solution, and extracted with ethyl acetate. The organic layer was successively washed with water and brine, dried, and concentrated, to thereby obtain the title compound (0.91 g) having the following physical properties.

Workup

  1. customthe reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was successively washed with water and brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9ec1c87a7cba46e6aae4812c5107099d
Source dataset
uspto-grants-2011_03
Patent number
US07906549B2

Reaction notes

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