Water → HCID 22241484, compound

HRID 892217Notes

Reaction equation

HRID 892217 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[C:3]=1[C:4](OC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1.CCOCC>[OH:5][CH2:4][C:3]1[C:2]([CH3:1])=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:12][O:13][C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22241441HCID 22241441, compound

Product 1

HCID 22241484HCID 22241484, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of methyl 2-methyl-6-[(3-hydroxy-phenoxy)-methyl]-benzoate (220 mg, 0.76 mmol, example 5) in THF (2 mL) is added lithium aluminum hydride solution (1.5 mL, 1 M in THF). The resulting solution is stirred for 10 min then warmed to room temperature and stirred for 40 min. This solution is then cooled to 0° C. and water (75 mL) added, dropwise, followed by sodium hydroxide solution (75 mL, SN) and water (75 mL). The resulting suspension is diluted with ether, filtered through celite and the solid washed thoroughly with methanol (until the solid is free of product by TLC analysis). The combined filtrates are concentrated under vacuum to give the title compound as a white solid. MS (EI) 244 (M)+.

Workup

  1. stirringstirred for 40 min
  2. temperatureThis solution is then cooled to 0° C.
  3. filtrationfiltered through celite
  4. washthe solid washed thoroughly with methanol (until the solid
  5. concentrationThe combined filtrates are concentrated under vacuum

Sources & evidence

ORD record
ord-068f83e716ae469fa9ba99c802e404a1
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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