Hydrochloric Acid → 2-Hydroxymethylchrysene

HRID 1762015

Reaction equation

HRID 1762015 reaction equation
[CH:1]1[C:18]2[CH:17]=[CH:16][C:15]3[C:6](=[CH:7][CH:8]=[C:9]4[C:14]=3[CH:13]=[CH:12][CH:11]=[CH:10]4)[C:5]=2[CH:4]=[CH:3][C:2]=1[C:19](OCC)=[O:20].[Li+].[BH4-].Cl>C1COCC1>[CH:1]1[C:18]2[CH:17]=[CH:16][C:15]3[C:6](=[CH:7][CH:8]=[C:9]4[C:14]=3[CH:13]=[CH:12][CH:11]=[CH:10]4)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:19][OH:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 15599324Ethyl chrysene-2-carboxylate

Product 1

HCID 155993232-HydroxymethylchryseneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl chrysene-2-carboxylate (20B, 10.1 g, 0.034 mol) in THF (500 mL) was treated with LiBH4 (Alfa, 4×0.5 g, 0.092 mol) under gentle reflux for 4 days. The reaction mixture was poured into ice and acidified carefully to pH 1 with 1M HCl. The precipitate was filtered and recrystallized from THF/hexane to afford 8.32 g (95%) of 2-chrysenemethanol mp 261°-262°, (C,H).

Workup

  1. temperatureunder gentle reflux for 4 days
  2. additionThe reaction mixture was poured into ice
  3. filtrationThe precipitate was filtered
  4. customrecrystallized from THF/hexane

Sources & evidence

ORD record
ord-b37c284ce8084a5da4815fcaad649bf5
Source dataset
uspto-grants-1989_05
Patent number
US04829090

Linked notes

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