Water → (3-Methoxy-1,2-phenylene)dimethanol

HRID 505252Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10](=[O:12])[O:9][CH2:8]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.C(Cl)Cl>C1COCC1>[OH:9][CH2:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:11]=1[CH2:10][OH:12]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 7-methoxy-3H-isobenzofuran-1-one (16.65 g, 101.4 mmol) in anhydrous THF (200 ml) was added at room temperature under an atmosphere of argon to a freshly prepared solution of LiAlH4 (7.70 g, 202.8 mmol, 2.0 equiv) in THF (100 ml). After 30 minutes at room temperature, TLC analysis indicated complete conversion. The reaction mixture was cooled to 0° C. and water was added dropwise until gas evolution ceased. Water (500 ml) and CH2Cl2 (500 ml) was added to form a white suspension. After filtration, the filtrate was extracted with CH2Cl2 (4 liters in total). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound (15.34 g, 90%) in adequate purity for direct use in the next transformation. 1H NMR (400 MHz, CDCl3): δ=7.27 (t, J=7.8 Hz, 1H), 6.96 (d, J=7.3 Hz, 1H), 6.89 (d, J=8.3 Hz, 1H), 4.83 (s, 2H); 4.72 (s, 2H), 3.85 (s, 3H), 2.8-2.6 (br s, 2H). MS (ES+): 169 (M+H)+.

Workup

customto form a white suspension
filtrationAfter filtration
extractionthe filtrate was extracted with CH2Cl2 (4 liters in total)
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7a5900d4dcb64bf0b912e8bad28fb2b4
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781438B2

Reaction notes

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