Hydrochloric Acid → 2-methoxyanthracene

HRID 414155Notes

Reaction equation

HRID 414155 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=O)[C:5]=2[CH:4]=1.[OH-].[Na+].Cl.[K+].[Br-]>[Zn].O>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 253877Potassium BromideHCID 4361739(10H)-Anthracenone, 2-methoxy-

Product 1

HCID 115358102-methoxyanthracene

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

A well-stirred mixture of 20 g zinc dust, 2 ml Fehling I solution, and 120 ml of water was added to a suspension of 8 g 2-methoxy-9-anthrone and 200 ml of 10% aqueous sodium hydroxide. The mixture was refluxed for 30 minutes and filtered hot to give a gray solid. The solid was heated on a steam bath and swirled vigorously while 120 ml of conc. hydrochloric acid were added drop by drop over a 40 min. period. A crude, slightly yellow solid was collected on a Buchner funnel, washed with 100 ml water and 50 ml methanol, and then crystallized from benzene twice to give 6.4 g (86%) of plate-like crystals: mp. 182.5°-183.5° C. (lit.* mp 163-165). IR (KBr): 1635, 1480, 1465, 1435, 1345, 1220-1175, 1300-1270, 1025, 950, 880, 800, 740 cm-1. 1H NMR (CDCl3 /TMS): δ8.3 (1 H, s, anthrancenyl meso proton), 8.2 (H, s, anthracenyl meso proton, 7.75-8.05 (3 H, m, oxyanthracenyl protons), 7.05-7.50 (4 H, m, oxyanthracenyl protons), 3.95 (3 H, s, ArOCH3).

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. filtrationfiltered hot
  3. customto give a gray solid
  4. temperatureThe solid was heated on a steam bath
  5. additionwere added drop by drop over a 40 min. period
  6. customA crude, slightly yellow solid was collected on a Buchner funnel
  7. washwashed with 100 ml water and 50 ml methanol
  8. customcrystallized from benzene twice
  9. customto give 6.4 g (86%) of plate-like crystals

Sources & evidence

ORD record
ord-280d17e4acb44ef48b9f4bf3df0e37fb
Source dataset
uspto-grants-1988_12
Patent number
US04790961

Reaction notes

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