Boron trifluoride → 10-(Hydroxymethyl)anthracene-9-carbaldehyde

HRID 2057559

Reaction equation

[O:1]1[CH2:3][C:2]21[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:10]1([CH2:18][O:17]1)[C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]2=1.B(F)(F)F.C(=O)(O)[O-].[Na+]>CCOCC>[OH:17][CH2:18][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:2]([CH:3]=[O:1])=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[CH:15]2

Participants

Conditions

Temperature: -45 °C

Procedure

To a solution of 500 mg. of the product of Example 1 in 50 ml. of anhydrous ether maintaining at -45° C. is added dropwise a solution of 0.060 ml. of boron trifluoride in 2.0 ml. of anhydrous ether. The reaction mixture is stirred at -45° C. for 10 minutes and then allowed to warm to -30° C. in 5 minutes. The reaction mixture is poured into a mixture of 20 ml. of cool saturated sodium bicarbonate solution and 30 ml. of ether. The ethereal solution is washed with an additional 20 ml. of saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate and filtered. The ether is removed to provide a yellow solid. The solid is recrystallized from acetonitrile to give 259 mg. of the desired product as yellow crystals, mp. 182°-184° C.

Workup

temperatureto warm to -30° C. in 5 minutes
additionThe reaction mixture is poured into a mixture of 20 ml
washThe ethereal solution is washed with an additional 20 ml
dry with materialof saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate
filtrationfiltered
customThe ether is removed
customto provide a yellow solid
customThe solid is recrystallized from acetonitrile
customto give 259 mg

Sources & evidence

ORD record: ord-473f31cc4b244f95b7a217b5bc64ab36
Source dataset: uspto-grants-1980_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04211726

Linked notes

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