Sodium Hydroxide → HCID 88170646, compound

HRID 634878Notes

Reaction equation

HRID 634878 reaction equation
[CH2:1]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH:24]=[O:25])=[CH:20]N(C)C)=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[OH-:26].[Na+]>C(O)C>[CH2:1]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH:24]=[O:25])=[CH:20][OH:26])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 88169897HCID 88169897, compound

Product 1

HCID 88170646HCID 88170646, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 21 in ethanol (75 ml) was hydrolysed with aqueous sodium hydroxide solution (60 ml, 25%). The reaction mixture was stirred and heated under reflux (3 h), cooled to room temperature and the ethanol removed in vacuo to yield an off-white solid which was filtered and washed thoroughly with water. The solid was suspended in a 50% ethanol/water mixture (150 ml) and acidified with concentrated hydrochloric acid. The suspended solid whitened in colour and was collected by filtration, then recrystallised from petroleum ether (bp 60-80° C.). Yield=3.97 g (38%).

Workup

  1. temperatureheated
  2. temperatureunder reflux (3 h)
  3. customthe ethanol removed in vacuo
  4. customto yield an off-white solid which
  5. filtrationwas filtered
  6. washwashed thoroughly with water
  7. filtrationThe suspended solid whitened in colour and was collected by filtration
  8. customrecrystallised from petroleum ether (bp 60-80° C.)

Sources & evidence

ORD record
ord-d0cb457a34ec4657b9480959005ba746
Source dataset
uspto-grants-2001_02
Patent number
US06184322B2

Reaction notes

Loading…