Chromanone → Chroman-4-ol

HRID 1296083Notes

Reaction equation

HRID 1296083 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([OH:11])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 68110ChromanoneHCID 4311764Sodium borohydride

Product 1

HCID 92890Chroman-4-olYield 956.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a MeOH (250 ml) solution of 4-chromanone (16.6 g, 11 mmol), at 0° C., was added NaBH4 (5.5 g, 145 mmol) in 1 g portions over a 30 min. period. After complete addition the mixture was stirred for 1 h with spontaneous warming. The reaction was quenched with the slow addition of aq. NH4Cl (100 ml). The MeOH was removed in vacuo and the residue extracted with Et2O (2×100 ml). The organic layers were dried over MgSO4 and treated with activated carbon. After filtration the Et2O was removed in vacuo to yield 15.8 g of chroman-4-ol as a clear oil. HRMS (ESI+) calcd for C9H10O2 m/z 150.0681 (M+H)+. Found 150.0679.

Workup

  1. additionAfter complete addition the mixture
  2. customThe reaction was quenched with the slow addition of aq. NH4Cl (100 ml)
  3. customThe MeOH was removed in vacuo
  4. extractionthe residue extracted with Et2O (2×100 ml)
  5. dry with materialThe organic layers were dried over MgSO4
  6. additiontreated with activated carbon
  7. filtrationAfter filtration the Et2O
  8. customwas removed in vacuo

Sources & evidence

ORD record
ord-d5528d32fd1744f582aa011ee8dd4aba
Source dataset
uspto-grants-2007_07
Patent number
US07244725B2

Reaction notes

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