Ethanol → HCID 21544760, compound

HRID 1606808Notes

Reaction equation

HRID 1606808 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]([CH2:17][CH3:18])=[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.CCOCC.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]([CH2:17][CH3:18])=[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 54123388HCID 54123388, compound

Product 1

HCID 21544760HCID 21544760, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 7268Diethyl OxalateSolvent

Procedure

A solution of 1-(2-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-p-ethylphenoxypropane (25.6 g) in diethyl oxalate (30 ml) was added to a suspension of sodium ethoxide, prepared from sodium (6.0 g) and ethanol (60 ml), in dry ether (400 ml). The mixture was heated under reflux for 1.5 hours and the greenish-brown residue was poured onto ice (200 g) and acidified with a solution of acetic acid (24 ml) in water (160 ml). The ether layer was separated after the addition of a further quantity of water (200 ml), and the aqueous layer was extracted with ether (3 × 50 ml), adding the extracts to the organic layer. The solvent was then removed and the residue dissolved in absolute ethanol (200 ml) to which hydrochloric acid (10 drops) was added. The solution was heated under reflux for 1 hour and the solvent was then removed to give a brownish oil from which crystals separated on standing overnight. These were filtered off, and washed with the minimum volume of ether to afford 1-(2-carbethoxy-chromon-5-yloxy)-2-hydroxy-3-p-ethylphenoxypropane (15.7 g) as a white solid, m.p. 80°-85°. A portion was recrystallized from aqueous ethanol to give white flakes, m.p. 84°-86°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. additionthe greenish-brown residue was poured onto ice (200 g)
  4. customThe ether layer was separated
  5. additionafter the addition of a further quantity of water (200 ml)
  6. extractionthe aqueous layer was extracted with ether (3 × 50 ml)
  7. additionadding the extracts to the organic layer
  8. customThe solvent was then removed
  9. dissolutionthe residue dissolved in absolute ethanol (200 ml) to which hydrochloric acid (10 drops)
  10. additionwas added
  11. temperatureThe solution was heated
  12. temperatureunder reflux for 1 hour
  13. customthe solvent was then removed
  14. customto give a brownish oil from which crystals
  15. customseparated
  16. filtrationThese were filtered off
  17. washwashed with the minimum volume of ether

Sources & evidence

ORD record
ord-11882c3ca43d41d3af1df8ad293bca3b
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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