Sodium Hydroxide → 3-m-Anisyl-1-propanol

HRID 413422Notes

Reaction equation

HRID 413422 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11](O)=[O:12])[CH:6]=[CH:7][CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 663363-(m-Methoxyphenyl)propionic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 961303-m-Anisyl-1-propanol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(3-Methoxyphenyl)propionic acid (see Example 1, Step J) (10.09 g, 0.058 mol) dissolved in anhydrous THF 60 mL) was added dropwise to a solution of LiAlH4 (1M in THF) (60 mL, 0.06 mol) in THF (60 mL) at ambient temperature under Ar. The resulting solution was stirred at reflux for 6 hr, then cooled to 0° C., treated dropwise with H2O (2.2 mL), 20% NaOH (1.7 mL), then H2O (6.62 mL). After stirring for 15 min, MgSO4 was added, stirring was continued for 15 min, the solids were filtered off, washed well with EtOAc, and the filtrate concentrated to dryness to give the title compound. MS (M+1) 167.1

Workup

  1. temperatureat reflux for 6 hr
  2. stirringAfter stirring for 15 min
  3. stirringstirring
  4. filtrationthe solids were filtered off
  5. washwashed well with EtOAc
  6. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-ffc645b176df43ff9b46a9bcbb782c1f
Source dataset
uspto-grants-2003_05
Patent number
US06566385B2

Reaction notes

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