Hydrochloric Acid → 3-Hydroxybenzo[b]naphtho[2,3-d]furan-6,11-dione

HRID 1660714Notes

Reaction equation

HRID 1660714 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[O-]CC.[Na+].Cl[C:14]1[C:15](=[O:26])[C:16]2[C:21]([C:22](=[O:25])[C:23]=1Cl)=[CH:20][CH:19]=[CH:18][CH:17]=2.Cl>C(O)C>[OH:2][C:1]1[CH:8]=[CH:7][C:6]2[C:23]3[C:22](=[O:25])[C:21]4[C:16]([C:15](=[O:26])[C:14]=3[O:5][C:4]=2[CH:3]=1)=[CH:17][CH:18]=[CH:19][CH:20]=4

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5054ResorcinolHCID 8342DichloneHCID 2723922Sodium ethoxide

Product 1

HCID 15125833-Hydroxybenzo[b]naphtho[2,3-d]furan-6,11-dioneYield 89.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Resorcinol (6.6 g, 60 mmol) in ethanol (80 mL) was added dropwise to a stirred ethanolic sodium ethoxide solution (prepared by dissolving 3.8 g of sodium metal in 120 mL of absolute ethanol) containing 2,3-dichloro-1,4-naphthoquinone (6.9 g, 30 mmol) at 0° C. After stirring at room temperature overnight, the black reaction mixture was acidified with 5N HCl at 0° C. The yellow solid that precipitated was collected by filtration, washed successively with water, methanol, diethyl ether and air-dried to give crude 12 as a deep yellow solid (7.1 g, 88%); mp>310° C. (lit.>300° C.);Cheng 1993 JMC TLC (chloroform/acetone, 8:1): Rf 0.47; νmax (KBr) 3400 (OH), 1670 and 1620 (C═O) cm−1; δH (400 MHz, DMSO-d6) 7.05 (1H, d, JC-5-H, C-4-H=8.54 Hz, C-4-H), 7.16 (1H, s, C-2-H), 7.2-7.7 (2H, m, C-8-H and C-9-H), 7.95 (1H, d, JC-4-H, C-5-H=8.5 Hz, C-5-H), 8.2-8.7 (2H, m, C-7-H and C-10-H) and 10.53 (1H, br s, exchanged with D2O, C-3-OH); MS m/z (FAB+) 265.1 [70, (M+H)+], 255.3 (75), 243.2 (30), 173.2 (100); MS m/z (FAB−) 263.1 [100, (M−H)−], 242.1 (20), 210.1 (25), 198.1 (45), 181.1 (35); Acc. MS (FAB+) 265.0502 C16H9O4 requires 265.0501.

Workup

  1. filtrationThe yellow solid that precipitated was collected by filtration
  2. washwashed successively with water, methanol, diethyl ether
  3. customair-dried

Sources & evidence

ORD record
ord-9aad2a4ebfd84648a673b2176dbbb6b7
Source dataset
uspto-grants-2011_10
Patent number
US08030296B2

Reaction notes

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