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Hydrochloric Acid → 1-Hydroxymethylfluoranthene

HRID 2255819
Notes
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Reaction equation

HRID 2255819 reaction equation
C[O:2][C:3]([C:5]1[C:19]2=[C:20]3[C:12]([C:13]4[C:18]2=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:11][CH:10]=[CH:9][C:8]3=[CH:7][CH:6]=1)=O.[Li+].[BH4-].C1COCC1.Cl>O>[OH:2][CH2:3][C:5]1[C:19]2=[C:20]3[C:12]([C:13]4[C:18]2=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:11][CH:10]=[CH:9][C:8]3=[CH:7][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 15050895Methyl-1-fluoranthenecarboxylate

Product 1

HCID 1544331-HydroxymethylfluorantheneYield 86%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

To a RB flask equipped with magnetic stirrer, condenser, and N2 inlet line with bubbler was added methyl-1-fluoranthenecarboxylate (3A, 71.54 g, 0.275 mol), LiBH4 (Aldrich, 100 g, 0.459 mol) and dry THF (1 L). The mixture was refluxed overnight, cooled and poured into H2O (2 L). The mixture was cautiously acidified with 1N HCl, filtered and the resulting solid washed with H2O (2×300 mL). After recrystallization (CH2Cl2 /hexane) and drying, 54.75 g (86%) of 1-hydroxymethylfluoranthene was obtained, mp 147°-185°, (C,H).

Workup

  1. customTo a RB flask equipped with magnetic stirrer, condenser, and N2 inlet line with bubbler
  2. temperatureThe mixture was refluxed overnight
  3. temperaturecooled
  4. filtrationfiltered
  5. washthe resulting solid washed with H2O (2×300 mL)
  6. customAfter recrystallization (CH2Cl2 /hexane)
  7. customdrying

Sources & evidence

ORD record
ord-ac9aedbe966c4395a1df85444ecf26f5
Source dataset
uspto-grants-1993_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05241107

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes