4-Hydroxy-1-indanone → 4-Hydroxyindan

HRID 2307882Notes

Reaction equation

HRID 2307882 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=O.C([BH3-])#N.[Na+]>ClC(Cl)C.[I-].[Zn+2].[I-]>[CH2:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:2]([OH:1])[C:3]=2[CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 5905474-Hydroxy-1-indanoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 742334-HydroxyindanYield 92.9%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 4-hydroxy-indan-1-one (5.0 g, 33.7 mmol), sodium cyanoborohydride (6.4 g, 101.1 mmol), and zinc iodide (32.3 g, 101.1 mmol) in dichloroethane, was heated at reflux for two hours. The reaction mixture was then filtered through 50 g SiO2 while still warm, eluting further with dichloroethane. The filtrate was collected and concentrated under vacuum. The residue was added to diethyl ether and the resulting white precipitate was filtered off. The filtrate was collected and concentrated in vacuo to give 4.2 g of the title compound with purity high enough for subsequent use. 400 MHz 1H NMR (DMSO-d6) δ 9.06 (s, 1H), 6.86 (t, 1H, J=7.8 Hz), 6.59 (d, 1H, J=7.8 Hz), 6.48 (d, 1H, J=7.8 Hz), 2.75 (t, 2H, J=7.3 Hz), 2.67 (t, 2H, J=7.3 Hz), 1.92 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for two hours
  3. filtrationThe reaction mixture was then filtered through 50 g SiO2
  4. temperaturewhile still warm
  5. washeluting further with dichloroethane
  6. customThe filtrate was collected
  7. concentrationconcentrated under vacuum
  8. additionThe residue was added to diethyl ether
  9. filtrationthe resulting white precipitate was filtered off
  10. customThe filtrate was collected
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-597a315ad7274ea8ae5ccb1ef9900ada
Source dataset
uspto-grants-2004_12
Patent number
US06833380B2

Reaction notes

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