Ethanol → HCID 21544794, compound

HRID 1606810Notes

Reaction equation

HRID 1606810 reaction equation
[C:1]([C:4]1[C:23]([OH:24])=[CH:22][CH:21]=[CH:20][C:5]=1[O:6][CH2:7][CH:8]([OH:19])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)(=[O:3])[CH3:2].[O-:25][CH2:26][CH3:27].[Na+].[Na].[CH2:30]([OH:32])[CH3:31]>C(OCC)(=O)C(OCC)=O.C1C=CC=CC=1.O.C(O)(=O)C>[C:26]([C:27]1[O:24][C:23]2[C:4]([C:1](=[O:3])[CH:2]=1)=[C:5]([O:6][CH2:7][CH:8]([OH:19])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)[CH:20]=[CH:21][CH:22]=2)([O:32][CH2:30][CH3:31])=[O:25]

Participants

9

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 54073604HCID 54073604, compound

Product 1

HCID 21544794HCID 21544794, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 241BenzeneSolventHCID 962WaterSolventHCID 7268Diethyl OxalateSolvent

Procedure

A suspension of 1-(2-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-p-cyanophenoxypropane (13.1 g) in diethyl oxalate (15 ml) was added to a suspension of sodium ethoxide, prepared from sodium (3.0 g) and ethanol (30 ml) in dry benzene (200 ml). The resulting mixture was heated under reflux for 2 hours, cooled, poured onto ice (100 g), and acidified with a solution of acetic acid (12 ml) in water (80 ml). The benzene layer was separated, and the aqueous layer extracted with ether (3 × 25 ml). The extracts were combined with the organic layer, the solvent was removed, and the residue was dissolved in absolute ethanol (100 ml) to which hydrochloric acid (5 drops) was added. The yellow solution was heated under reflux for 1 hour and the solvent removed to give a yellow solid. Recrystallization from ethanol gave 1-(2-carbethoxychromon-5-yloxy)-2-hydroxy-3-p-cyanophenoxypropane (5.4 g) as a beige solid m.p. 137°-139° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. additionpoured onto ice (100 g)
  5. customThe benzene layer was separated
  6. extractionthe aqueous layer extracted with ether (3 × 25 ml)
  7. customthe solvent was removed
  8. dissolutionthe residue was dissolved in absolute ethanol (100 ml) to which hydrochloric acid (5 drops)
  9. additionwas added
  10. temperatureThe yellow solution was heated
  11. temperatureunder reflux for 1 hour
  12. customthe solvent removed
  13. customto give a yellow solid
  14. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-9494b5b8654b4159aafcb10a8a68bb31
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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