Potassium Carbonate → HCID 86662491, compound

HRID 1892034Notes

Reaction equation

HRID 1892034 reaction equation
C(OC1C=CC2C(=CC=CC=2)C=1C=NO)C1OC1.[OH:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]=1[CH:30]=[O:31].C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45]>CN(C)C=O.O>[CH2:47]([O:46][C:44]([CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][O:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]=1[CH:30]=[O:31])=[O:45])[CH3:48]

Participants

7

Procedure

As shown in Chemical Formula 4, in 20 mL of DMF (N,N-dimethylformamide), 1.09 g (6.33 mmol) of 2-hydroxy-1-naphthoaldehyde (1) and 1.22 g (8.86 mmol) of potassium carbonate were dissolved and the resultant reaction solution was stirred for 1 hour. To the reaction solution, 1.94 g (8.72 mmol) of ethyl 6-bromohexanoate (5) was added and the resultant reaction mixture was stirred at 100° C. for 13 hours to effect the reaction. Then, to the reaction solution, 50 mL of water was added and the reaction mixture was extracted with 50 mL of ethyl acetate. The organic phase was washed with each of 50 mL of pure water and 50 mL of Brine three times and was dried over MgSO4, and the solvent thereof was concentrated under reduced pressure. The resultant green crude product was recrystallized in hexane-AcOEt (hexane-ethyl acetate) to obtain 1.67 g (yield: 84%) of 2-[5-(ethoxycarbonyl)pentyloxy]-1-naphthoaldehyde (6) as a plate-shaped crystal.

Workup

  1. customthe resultant reaction solution
  2. customthe resultant reaction mixture
  3. stirringwas stirred at 100° C. for 13 hours
  4. customthe reaction
  5. extractionthe reaction mixture was extracted with 50 mL of ethyl acetate
  6. washThe organic phase was washed with each of 50 mL of pure water and 50 mL of Brine three times
  7. dry with materialwas dried over MgSO4
  8. concentrationthe solvent thereof was concentrated under reduced pressure
  9. customThe resultant green crude product was recrystallized in hexane-AcOEt (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2663ecf32e5d4074be23b0d4d5d9f537
Source dataset
uspto-grants-2013_08
Patent number
US08507611B2

Reaction notes

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