Hydrochloric Acid → 3-Hydroxymethylchrysene

HRID 1762012Notes

Reaction equation

HRID 1762012 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]=[C:3]([C:19](OCC)=[O:20])[CH:2]=1.[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]=[C:3]([CH2:19][OH:20])[CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 15599328Ethyl chrysene-3-carboxylate2×

Product 1

HCID 155993273-HydroxymethylchryseneYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl chrysene-3-carboxylate ((19E 17.7 g, 0.059 mol) in 40 mL THF was treated with LiBH4 (Morton Thiokol, Inc.-Alfa Products, PO Box 299, 152 Andover St., Danvers, MA 01923, 2.7 g, 0.12 mol) in three portions then refluxed for 3 days. The reaction mixture was poured into ice and acidified carefully to pH 1 with 1N HCl. The precipitate was filtered and recrystallized from THF/hexane to afford 14.98 g (98%) of 3-chrysenemethanol mp 187°-189°, (C,H).

Workup

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

Sources & evidence

ORD record
ord-18c5961ba8dc4e50b903284dd460220f
Source dataset
uspto-grants-1989_05
Patent number
US04829090

Reaction notes

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