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

HRID 1968764Notes

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-4a73947df006476db2b16a4441c820fa
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426440B2

Reaction notes

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