2-Acetylhydroquinone → HCID 69403676, compound

HRID 1868579Notes

Reaction equation

HRID 1868579 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li].C([O:13][C:14](=O)[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:17]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:16]=1)C.[CH3:38][C:39]([C:41]1[CH:46]=[C:45]([OH:47])[CH:44]=[CH:43][C:42]=1[OH:48])=[O:40]>O1CCCC1>[CH2:30]([O:29][C:17]1[CH:16]=[C:15]([C:14](=[O:13])[CH2:38][C:39]([C:41]2[CH:46]=[C:45]([OH:47])[CH:44]=[CH:43][C:42]=2[OH:48])=[O:40])[CH:20]=[CH:19][C:18]=1[O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 102792-AcetylhydroquinoneHCID 11325933ethyl-3,4-dibenzyloxybenzoateHCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 69403676HCID 69403676, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 20% lithiumhexamethyldisilazane in tetrahydrofuran (200.8 mL, 240 mmol), 2,5-dihydroxy acetophenone, 15 (9.12 g, 60 mmol) in tetrahydrofuran (150 mL) and ethyl-3,4-dibenzyloxy benzoate, 9 (21.7 g, 60 mmol) in tetrahydrofuran (100 mL) were reacted to afford 18, 1-(3,4-bis-benzyloxy-phenyl)-3-(2,5-dihydroxy-phenyl)-propane-1,3-dione (41 g), which was cyclized with Dowex-H+(12 g) in 2-propanol (300 mL) in a similar way as described for 22 to afford 24. Yield 12 g (44%); mp 196-197° C.; MS (FAB) 451 (M++1); IR (KBr) 3419, 1621; 1H NMR (200 MHz, DMSO-d6) δ 10.08 (s, 1H), 7.75 (s, 1H), 7.69 (d, J=8.7 Hz, 1H), 7.63 (s, 1H), 7.55-7.22 (m, 13H), 6.94 (s, 1H), 5.30 (s, 2H), 5.27 (s, 2H).

Sources & evidence

ORD record
ord-02525d9cc34b457bb1cbe3d495294bc6
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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