Water → (2,3-Bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol

HRID 253240Notes

Reaction equation

HRID 253240 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:15]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:14][CH:13]=[CH:12][C:7]=1[C:8](OC)=[O:9].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:15]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:14][CH:13]=[CH:12][C:7]=1[CH2:8][OH:9]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66888836Methyl 2,3-bis{[2-(methyloxy)ethyl]oxy}benzoate

Product 1

HCID 66889790(2,3-Bis{[2-(methyloxy)ethyl]oxy}phenyl)methanolYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 2,3-bis{[2-(methyloxy)ethyl]oxy}benzoate (2.0 g, 7.03 mmol) in dry THF (10 mL) was added dropwise a 1M solution of lithium aluminum hydride in THF (7.0 mL), and the resulting mixture was stirred at rt for 1 h. Then, water (0.27 mL) was added slowly, followed by 15% aqueous sodium hydroxide (0.27 mL), and more water (0.81 mL). The mixture was filtered, the filter cake washed with ethyl acetate, and the combined filtrate was concentrated. Column chromatography on silica (1:1 hexanes/ethyl acetate) gave (2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol (1.13 g, 63% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ6.96 (dd, 1H), 6.86 (m, 2H), 4.60 (d, 1H), 4.33 (m, 2H), 4.24 (t, 1H), 4.13 (m, 2H), 3.75 (m, 2H), 3.70 (m, 2H), 3.43 (s, 6H).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake washed with ethyl acetate
  3. concentrationthe combined filtrate was concentrated

Sources & evidence

ORD record
ord-fc99ee0a0a8c439e8b95bab77c111a7d
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

Loading…