Ethanol → HCID 68138656, compound

HRID 1606802Notes

Reaction equation

HRID 1606802 reaction equation
[C:1]([C:4]1[C:22]([OH:23])=[CH:21][CH:20]=[CH:19][C:5]=1[O:6][CH2:7][CH:8]([OH:18])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])(=[O:3])[CH3:2].[O-:24][CH2:25][CH3:26].[Na+].[Na].C([OH:31])C>C(OCC)(=O)C(OCC)=O.C1C=CC=CC=1>[C:25]([C:26]1[O:23][C:22]2[C:4]([C:1](=[O:3])[CH:2]=1)=[C:5]([O:6][CH2:7][CH:8]([OH:18])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[CH:19]=[CH:20][CH:21]=2)([OH:31])=[O:24]

Participants

7

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21544835HCID 21544835, compound

Product 1

HCID 68138656HCID 68138656, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 7268Diethyl OxalateSolvent

Procedure

A solution of 1-(2-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-o-cresyloxypropane (18.96 g) in diethyl oxalate (22.5 ml) was added to a suspension of sodium ethoxide, prepared from sodium (4.5 g) and ethyl alcohol (4.5 ml), in benzene (150 ml). The mixture was heated under reflux for 1.5 hours, cooled, and filtered after pouring into ether (150 ml). The residual solid was washed with ether and dried, and then added to a mixture of glacial acetic acid (120 ml) and concentrated hydrochloric acid (45 ml) and heated under reflux for 1 hour. After cooling, the residue was poured with stirring into cold water (1 L). The precipitated gum solidified after decanting the liquor and washing with water. The beige solid was recrystallized twice from ethyl acetate and finally from alcohol to give 1-(2-carboxy-chromon-5-yloxy)-2-hydroxy-3-o-cresyloxypropane (6.0g) as an off white solid, m.p. 95°-97° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. additionafter pouring into ether (150 ml)
  6. washThe residual solid was washed with ether
  7. customdried
  8. additionadded to a mixture of glacial acetic acid (120 ml) and concentrated hydrochloric acid (45 ml)
  9. temperatureheated
  10. temperatureunder reflux for 1 hour
  11. temperatureAfter cooling
  12. additionthe residue was poured
  13. customThe precipitated gum solidified after decanting the liquor
  14. washwashing with water
  15. customThe beige solid was recrystallized twice from ethyl acetate and finally from alcohol

Sources & evidence

ORD record
ord-461c14402daf471ea1136e16106fd4ae
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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