Water → HCID 20684020, compound

HRID 2400547Notes

Reaction equation

HRID 2400547 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][C:9]1[CH:19]=[CH:18][C:12]([C:13](OCC)=[O:14])=[CH:11][CH:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][OH:14])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59504711HCID 59504711, compound

Product 1

HCID 20684020HCID 20684020, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-[2-(2-methoxyethoxy)ethoxy]benzoate (Step 1, 1.0 g, 3.73 mmol) in 18 mL dry THF was added dropwise a solution of lithium aluminium hydride (1M in THF, 5.6 mL, 5.59 mmol) at 0° C. After the addition was completed, stirring of the reaction mixture was continued for 1 h at rt. Then, 1 g Celite was added, as was 5 mL water with caution. After the addition of sodium hydroxide (1N aq., 2 mL), the precipitate which had formed was removed by filtration. After some washing of the precipitate with ethyl acetate, the organic layer was separated from the filtrate and the aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed in vacuo to yield the title compound (710 mg, 84%): 1H NMR (400 MHz, CDCl3) δ 7.28 (d, 2H), 6.90 (d, 2H), 4.61 (s, 2H), 4.14 (t, 2H), 3.86 (t, 2H), 3.72 (t, 2H), 3.58 (t, 2H), 3.39 (s, 3H).

Workup

  1. additionAfter the addition
  2. additionThen, 1 g Celite was added
  3. customthe precipitate which had formed
  4. customwas removed by filtration
  5. washAfter some washing of the precipitate with ethyl acetate
  6. customthe organic layer was separated from the filtrate
  7. extractionthe aqueous layer was extracted with additional ethyl acetate
  8. washThe combined organic layers were washed with water and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationAfter filtration
  11. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f59110eed5424723a66cca4b99b51c4f
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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