Water → 1-Pyrenemethanol

HRID 1440185

Reaction equation

HRID 1440185 reaction equation
[C:1]1([CH:17]=[O:18])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.[BH4-].[Na+].O>C(O)C>[OH:18][CH2:17][C:1]1[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2328481-PyrenecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 1049771-Pyrenemethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of pyrene carboxaldehyde (9.6 g, 42 mmol) in ethanol (50 mL) was added NaBH4 (2 g) and the mixture was stirred at room temperature for 6 hours. Water (100 mL) was added and the mixture was extracted with ether (2×50 mL). The organic layer was dried over MgSO4, and the solvent evaporated under reduced pressure to give a light-yellow solid which was recrystallized from ethyl acetate to afford prisms, m.p. 125°-126° C., yield: 8.3 g, 86%.

Workup

  1. extractionthe mixture was extracted with ether (2×50 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent evaporated under reduced pressure
  4. customto give a light-yellow solid which
  5. customwas recrystallized from ethyl acetate
  6. customto afford prisms, m.p. 125°-126° C., yield: 8.3 g, 86%

Sources & evidence

ORD record
ord-7c454cfe4a7e4bb8bdebc150567edb97
Source dataset
uspto-grants-1996_03
Patent number
US05498549

Linked notes

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