Hydrochloric Acid → 2-Anthracenemethanol

HRID 1381803Notes

Reaction equation

HRID 1381803 reaction equation
[OH:1][CH2:2][C:3]1[CH:16]=[CH:15][C:14]2[C:13](=O)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=O)[C:5]=2[CH:4]=1.[NH4+].[OH-].Cl>CC(O)C.[Zn]>[CH:4]1[C:5]2[C:14](=[CH:13][C:12]3[C:7]([CH:6]=2)=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:15]=[CH:16][C:3]=1[CH2:2][OH:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 870142-(Hydroxymethyl)anthraquinone

Product 1

HCID 12014782-Anthracenemethanol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3776IsopropanolSolvent

Procedure

To a 2 L 3-neck flask fitted with condenser, thermometer and overhead stirrer was added 2-(hydroxymethyl)anthraquinone (Aldrich, 20 g, 0.084 mol), Zn dust (Mallinckrodt, 50 g, 0.765 mol), CuSO4.5H2O (Mallinckrodt, 0.5 g), and 28% NH4OH (Mallinckrodt, 600 mL). The temperature was increased to 80°, and the initial dark-red color faded (about 3 h). After refluxing for an additional 30 min, the mixture was filtered. The filtrate was treated with conc. HCl until acidic, and the resulting precipitate collected. The zinc solid was extracted with EtOAc until the washings were clear, and the EtOAc removed to give an oil. The oil and the precipitate were added to a mixture of conc. HCl (12 ml) in i-PrOH (1200 mL). This solution was concentrated by rotary evaporation to near dryness and CH3OH (100 mL) was added to give after filtration and drying 13.48 g (77%) of (2-anthracenyl)methanol mp 218°-221° (lit mp 223°-224°, P. Arjunan and K. D. Berlin, Org. Prep. and Procedure., 13(5), 368 (1981)).

Workup

  1. customTo a 2 L 3-neck flask fitted with condenser
  2. temperatureThe temperature was increased to 80°
  3. custom(about 3 h)
  4. temperatureAfter refluxing for an additional 30 min
  5. filtrationthe mixture was filtered
  6. additionThe filtrate was treated with conc. HCl until acidic, and the resulting precipitate
  7. customcollected
  8. extractionThe zinc solid was extracted with EtOAc until the washings
  9. customthe EtOAc removed
  10. customto give an oil
  11. concentrationThis solution was concentrated by rotary evaporation
  12. additionwas added
  13. customto give
  14. filtrationafter filtration
  15. dry with materialdrying 13.48 g (77%) of (2-anthracenyl)methanol mp 218°-221° (lit mp 223°-224°, P. Arjunan and K. D. Berlin, Org. Prep. and Procedure., 13(5), 368 (1981))

Sources & evidence

ORD record
ord-525e775b65bf47a9b7d22cb600602bd9
Source dataset
uspto-grants-1989_02
Patent number
US04803221

Reaction notes

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