Hydrochloric Acid → 10-Chloro-1-anthracenemethanol

HRID 2413661Notes

Reaction equation

HRID 2413661 reaction equation
[Cl:1][C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:16](OCC)=[O:17].[Li+].[BH4-].Cl>C1COCC1>[Cl:1][C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[CH2:16][OH:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 21276219Ethyl 10-chloroanthracene-1-carboxylate

Product 1

HCID 1337541110-Chloro-1-anthracenemethanolYield 81.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 10-chloroanthracene-1-carboxylate (37B, 14.86 g, 0.052 mol) in THF (300 mL) was treated with LiBH4 (Alfa, 1.14 g, 0.052 mol) and refluxed for 16 h. The reaction mixture was poured into ice water and acidified with conc. HCl to pH=2. The solid was filtered, washed with H2O (500 mL), air dried and then chromatographed on a plug of SiO2 (500 g) using EtOAc as the eluting solvent. The solvent was removed by rotary evaporation to give a solid, which was crystallized from CCl4 to give 10.3 g (81%) of 10-chloro-1-anthracenemethanol mp 138°-140°, (C, H, Cl).

Workup

  1. temperaturerefluxed for 16 h
  2. filtrationThe solid was filtered
  3. washwashed with H2O (500 mL), air
  4. customdried
  5. customchromatographed on a plug of SiO2 (500 g)
  6. customThe solvent was removed by rotary evaporation
  7. customto give a solid, which
  8. customwas crystallized from CCl4

Sources & evidence

ORD record
ord-cbe15ca71f714fb2b262eed1590553cb
Source dataset
uspto-grants-1988_01
Patent number
US04719049

Reaction notes

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