Sodium Carbonate → HCID 72468931, compound

HRID 2093012Notes

Reaction equation

HRID 2093012 reaction equation
[CH:1]([O:4][C:5]1[C:12]([CH3:13])=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[CH3:14])([CH3:3])[CH3:2].Cl.[NH2:16][OH:17].C([O-])([O-])=O.[Na+].[Na+]>CCO.CCOC(C)=O>[CH:1]([O:4][C:5]1[C:12]([CH3:13])=[CH:11][C:8]([CH:9]=[N:16][OH:17])=[CH:7][C:6]=1[CH3:14])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 19363071HCID 19363071, compound

Product 1

HCID 72468931HCID 72468931, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(Isopropoxy)-3,5-dimethylbenzaldehyde (1.98 g, 10.3 mmol) in EtOH (60 mL) was heated to 60° C. with hydroxylamine hydrochloride (2.4 M aq. solution, 5.2 mL, 1.2 eq.) and Na2CO3 (1.2 M solution, 5.2 mL, 0.6 eq.) at room temperature for 2 hours. The reaction was transferred to a separatory funnel, diluted with EtOAc; the organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated to yield 710 mg (3.24 mmol) of 4-(isopropoxy)-3,5-dimethylbenzaldehyde oxime as a light yellow oil. 1H-NMR (500 MHz, CDCl3): 8.10 (s, 1H), 7.23 (s, 2H), 4.29-4.18 (m, 1H), 2.29 (s, 6H), 1.29 (d, 6H).

Workup

  1. customThe reaction was transferred to a separatory funnel
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-20a9685496744990abe2e34f41f8a8e6
Source dataset
uspto-grants-2013_05
Patent number
US08440706B2

Reaction notes

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