Benzaldehyde → HCID 69497995, compound

HRID 495320

Reaction equation

HRID 495320 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:7].[Na+].[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1>C(O)C.O>[O:7]1[CH2:5][CH2:4][CH2:3][CH2:2][CH:1]1[O:6][C:13]1[CH:14]=[CH:15][C:10]([CH:9]=[C:2]2[CH2:3][CH2:4][C:5](=[CH:28][C:27]3[CH:30]=[CH:31][C:24]([O:23][CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][O:17]4)=[CH:25][CH:26]=3)[C:1]2=[O:6])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 8452CyclopentanoneHCID 14798Sodium HydroxideHCID 112527364-(2-Tetrahydro-2H-pyranoxy)benzaldehyde

Product 1

HCID 69497995HCID 69497995, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Cyclopentanone (8.8 ml, 0.099 mol) was dissolved in ethanol (12 ml) and added to NaOH dissolved in water (25 ml) and ethanol (7 ml), and was left to stir for 25 min. This was then added to the THP protected benzaldehyde from 1CW01 (46.12 g, 0.22 mol), and the mixture was left to stir at room temperature for approximately 16 hours. A solid precipitate was isolated by vacuum filtration, washed with water (2×50 ml) and then ethanol (4×40 ml). This solid was recrystallised from ethanol to give a yellow solid (33.74 g, 74%).

Workup

  1. additionThis was then added to the THP
  2. waitthe mixture was left
  3. stirringto stir at room temperature for approximately 16 hours
  4. customA solid precipitate was isolated by vacuum filtration
  5. washwashed with water (2×50 ml)
  6. customThis solid was recrystallised from ethanol

Sources & evidence

ORD record
ord-0dc7a94483894b17b716ed6beacbeb41
Source dataset
uspto-grants-2005_09
Patent number
US06939479B2

Linked notes

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