Hydrochloric Acid → 1,4-Dimethoxyanthracene

HRID 2306904

Reaction equation

O[C:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]([OH:16])=[CH:4][CH:3]=1.I[CH3:18].CN([CH:22]=[O:23])C.Cl>O>[CH3:18][O:16][C:5]1[C:6]2[C:15](=[CH:14][C:13]3[C:8]([CH:7]=2)=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:2]([O:23][CH3:22])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a 0.275 g (11.0 mmol) of pre-washed (with distilled diethyl ether) sodium hydride under argon were added 1.00 g (4.80 mmol) of 1,4-dihydroxyanthracene, 0.75 mL (12.0 mmol) of iodomethane, and 10 mL of DMF (distilled over CaH2). The solution was stirred at 25° C. for 1.5 h, diluted with 20 mL of water, and acidified with 6 N HCl (pH ˜2). The mixture was extracted three times with ethyl acetate, and the combined extract was washed twice with water, and brine, dried (MgSO4), concentrated to give 1.07 g (94% yield) of compound 2. Recrystallization from ether:hexane (1:1) gave 0.89 g (78% yield) of yellow solids: mp 132-133° C. (Lit.6 134-136° C.); MS, FAB, m/z 239 (M+1), 238 (M+); 1H NMR d 8.70 (s, 2H, C9,10H), 7,97 (dd, J=6.1, 3.6 Hz, 2H, C5,8H), 7.40 (dd, J=6.6, 3.2 Hz, 2H, C6,7H ), 6.55 (s, 2H, C2,3H), 3.97 (s, 6H, OCH3); 13C NMR d 149.5 (s, C8a,10a), 131.5 (s, C4a,9a), 128.5 (d, C9,10), 125.5 (d, C5,8), 120.7 (d, C6,7), 100.9 (d, C2,3), 55.6 (s, OCH3).

Workup

washTo a 0.275 g (11.0 mmol) of pre-washed (with distilled diethyl ether) sodium hydride under argon
extractionThe mixture was extracted three times with ethyl acetate
extractionthe combined extract
washwas washed twice with water, and brine
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-bc3c39ff19b445d39a69c2d89f9a6d4f
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06828450B2

Linked notes

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