Sodium Hydroxide → HCID 66890573, compound

HRID 253271Notes

Reaction equation

HRID 253271 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]=1[O:12][CH3:13])[C:5](OC)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C(OCC)(=O)C.C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:9]=[C:10]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:11]=1[O:12][CH3:13]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 66890793HCID 66890793, compound

Product 1

HCID 66890573HCID 66890573, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl 3-fluoro-4-(methyloxy)-5-[(phenylmethyl)oxy]benzoate (3.54 g, 12.2 mmol.) was taken into anhydrous THF under a nitrogen atmosphere and the resulting solution was cooled to 0° C. A solution of lithium aluminum hydride (1.0M in THF, 20 mL) was slowly added and the solution was allowed to stir an additional 30 minutes at 0° C. Ethyl acetate (10 mL) was then slowly added followed by slow addition of 50% aqueous sodium hydroxide in portions until a granular precipitate was formed. Addition of anhydrous magnesium sulfate followed by filtration and washing the solid with ethyl ether then concentration of the combined organic layers gave an oily residue. Purification by silica gel flash chromatography using 2:1 hexanes:ethyl acetate as eluent provided {3-fluoro-4-(methyloxy)-5-[(phenylmethyl)oxy]phenyl}methanol (2.69 g, 84% yield) as a colorless oil after concentration of the pure fractions and drying in vacuo. GCMS for C15H15O3F: 262 (M+).

Workup

  1. customwas formed
  2. filtrationfollowed by filtration
  3. washwashing the solid with ethyl ether
  4. customconcentration of the combined organic layers gave an oily residue
  5. customPurification by silica gel flash chromatography

Sources & evidence

ORD record
ord-a7cdcabae00e4d58bbebf21a0dced779
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

Loading…