Sodium Hydroxide → HCID 18915232, compound

HRID 1292455Notes

Reaction equation

HRID 1292455 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][C:19]=1[CH:20]=[O:21])[N:8]([CH2:11][CH2:12][O:13]C(=O)C)[CH2:9][CH3:10])(=O)C.[OH-].[Na+]>CO.O>[CH2:9]([N:8]([CH2:11][CH2:12][OH:13])[C:7]1[CH:17]=[CH:18][C:19]([CH:20]=[O:21])=[C:5]([OH:4])[CH:6]=1)[CH3:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18915239HCID 18915239, compound

Product 1

HCID 18915232HCID 18915232, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 29.8 g (0.1 mole) of 3-acetoxy-N-(2-acetoxyethyl)-N-ethyl-4-formylaniline in 175 mL of methanol was added a solution of 17.5 g of sodium hydroxide in 175 mL of water. The mixture was stirred at room temperature overnight. Most of the methanol in the reaction mixture was evaporated with a rotary evaporator and the residue was diluted to 300 mL with water. The pH was adjusted to 6.5-7.0 by adding conc. HC1 (ca. 15-20 mL) slowly. The mixture was then extracted with ether (400 mL×3). The combined ether extracts were dried over MgSO4 and evaporated with a rotary evaporator to give 20.19 g (95%) of the product.

Workup

  1. customMost of the methanol in the reaction mixture was evaporated with a rotary evaporator
  2. additionthe residue was diluted to 300 mL with water
  3. additionby adding conc. HC1 (ca. 15-20 mL) slowly
  4. extractionThe mixture was then extracted with ether (400 mL×3)
  5. dry with materialThe combined ether extracts were dried over MgSO4
  6. customevaporated with a rotary evaporator

Sources & evidence

ORD record
ord-936405dc53774fd5b303ec1a14dc57e5
Source dataset
uspto-grants-1998_05
Patent number
US05756740

Reaction notes

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