4-Hydroxybenzaldehyde → Cyclamen aldehyde

HRID 529974Notes

Reaction equation

HRID 529974 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].O[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.[C:14](=O)([O-])[O-].[K+].[K+].[C:20](#N)[CH3:21]>>[CH3:3][CH:2]([C:1]1[CH:7]=[CH:6][C:13]([CH2:12][CH:9]([CH:10]=[O:11])[CH3:8])=[CH:21][CH:20]=1)[CH3:14]

Participants

5

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6342AcetonitrileHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 517827Cyclamen aldehyde

Procedure

Compound 1205 may be prepared by reacting allyl bromide (79.2 g, 656 mmol) and 4-hydroxybenzaldehyde A (40.0 g, 328 mmol) in the presence of potassium carbonate (90.6 g, 656 mmol) in acetonitrile (400 mL). The reaction is stirred at ambient temperature under an atmosphere of nitrogen for 4 hours. The reaction is filtered, washed with acetonitrile (200 mL), and concentrated in-vacuo. The residue is chromatographed on silica gel using a gradient of ethyl acetate from 10% to 30% in hexanes to give 50.0 g of aldehyde B as a colorless oil. LC/MS [M+H+] 163.2 (100), 2.85 min; 1H NMR (300 MHz, DMSO-d6) δ ppm 4.67 (d, J=5.03 Hz, 2H) 5.33 (dd, J=23.98, 1.51 Hz, 2H) 6.03 (dt, J=22.39, 5.07 Hz, 1H) 7.12 (d, J=8.72 Hz, 2H) 7.85 (d, J=8.38 Hz, 2H) 9.86 (s, 1H).

Workup

  1. filtrationThe reaction is filtered
  2. washwashed with acetonitrile (200 mL)
  3. concentrationconcentrated in-vacuo
  4. customThe residue is chromatographed on silica gel using a gradient of ethyl acetate from 10% to 30% in hexanes

Sources & evidence

ORD record
ord-ac7ce572824442d79b44c380359a45ea
Source dataset
uspto-grants-2016_05
Patent number
US09351964B2

Reaction notes

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