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

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

Reactant 3

HCID 8028Tetrahydrofuran

HCID 21226445Aluminium lithium hydride

HCID 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).