Water → 4H-1,3-Benzodioxin-6-methanol, 2,2,4,4-tetrafluoro-

HRID 881099Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]2[O:19][C:18]([F:21])([F:20])[O:17][C:16]([F:23])([F:22])[C:15]=2[CH:24]=1)=O.O.[OH-].[Na+]>C1COCC1>[F:21][C:18]1([F:20])[O:17][C:16]([F:22])([F:23])[C:15]2[CH:24]=[C:11]([CH2:9][OH:8])[CH:12]=[CH:13][C:14]=2[O:19]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of LAH (2.14 g, 56.4 mmol) in dry THF (200 mL) was added dropwise a solution of 2,2,4,4-tetrafluoro-4H-benzo[1,3]dioxine-6-carboxylic acid methyl ester (7.50 g, 28.2 mmol) in dry THF (50 mL) at 0° C. After being stirred at 0° C. for 1 h, the reaction mixture was treated with water (2.14 g) and 10% NaOH (2.14 mL). The slurry was filtered and washed with THF. The combined filtrates were evaporated to dryness to give the crude (2,2,4,4-tetrafluoro-4H-benzo[1,3]dioxin-6-yl)-methanol (6.5 g), which was used directly in the next step. 1H NMR (CDCl3, 300 MHz) δ 7.64 (s, 1 H), 7.57-7.60 (m, 1 H), 7.58 (d, J=8.7 Hz, 1 H), 4.75 (s, 2 H).

Workup

filtrationThe slurry was filtered
washwashed with THF
customThe combined filtrates were evaporated to dryness

Sources & evidence

ORD record: ord-2c558475d9da438ea9fe0accf502cece
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993600B2

Reaction notes

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