Tetrahydrofuran → (3,4-Bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol

HRID 253246Notes

Reaction equation

HRID 253246 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[C:9](OC)=[O:10].[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:9][OH:10])[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 45108175Methyl 3,4-bis(2-methoxyethoxy)benzoate

Product 1

HCID 66891044(3,4-Bis{[2-(methyloxy)ethyl]oxy}phenyl)methanolYield 82.1%

Procedure

To a solution of methyl 3,4-bis{[2-(methyloxy)ethyl]oxy}benzoate, (1.1 g, 3.9 mmol) at 0° C. was added a solution of lithium aluminum hydride in tetrahydrofuran (1.0M, 5.0 mL, 5.0 mmol) and the resulting mixture was stirred for one hour. It was then quenched with ethyl acetate (2 mL) and 5% sodium hydroxide solution (2 mL), diluted with ether (100 mL), and filtered. The filtrate was washed water and brine (100 mL each), dried over sodium sulfate, filtered and concentrated to give (3,4-bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol (0.82 g, 3.2 mmol, 82% yield). 1H NMR (400 MHz, CDCl3): 6.93 (s, 1H), 6.87 (s, 2H), 4.59 (s, 2H), 4.16-4.13 (m, 4H), 3.77-3.74 (m, 4H), 3.44 (s, 6H).

Workup

  1. customIt was then quenched with ethyl acetate (2 mL) and 5% sodium hydroxide solution (2 mL)
  2. additiondiluted with ether (100 mL)
  3. filtrationfiltered
  4. washThe filtrate was washed water and brine (100 mL each)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-11674d1ec460469cb9389234f4b37d22
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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