Ethanol → HCID 86733363, compound

HRID 1606812Notes

Reaction equation

HRID 1606812 reaction equation
[C:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][CH:10](O)[CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][C:5]=1[OH:22])(=[O:3])[CH3:2].[O-][CH2:24]C.[Na+].[Na].C(O)C.C(OCC)(=O)[C:32]([O:34]CC)=[O:33]>C1C=CC=CC=1>[C:32]([CH:10]([CH2:11][O:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:9][O:8][C:7]1[CH:6]=[C:5]2[C:4]([C:1](=[O:3])[CH:2]=[CH:24][O:22]2)=[CH:21][CH:20]=1)([OH:34])=[O:33]

Participants

7

Reactant 5

HCID 702EthanolHCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21544793HCID 21544793, compound

Product 1

HCID 86733363HCID 86733363, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1-(4-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-phenoxy-propane (6.04 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 benzene (50 ml). The mixture was heated under reflux for 1.5 hours, then cooled and filtered. The residual yellow sodium salt was washed with ether, dried, and dissolved in a mixture of glacial acetic acid (80 ml) and concentrated hydrochloric acid (30 ml). This solution was heated under reflux for 1 hour, cooled, and poured with stirring into cold water (500 ml). The precipitated solid (6.0 g) was filtered off and crystallized from methanol to give 1-(2-carboxychromon-7-yloxy-3-phenoxypropane (4.3 g) as an off-white solid, m.p. 222°-223.5°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe residual yellow sodium salt was washed with ether
  6. customdried
  7. dissolutiondissolved in a mixture of glacial acetic acid (80 ml) and concentrated hydrochloric acid (30 ml)
  8. temperatureThis solution was heated
  9. temperatureunder reflux for 1 hour
  10. temperaturecooled
  11. additionpoured
  12. filtrationThe precipitated solid (6.0 g) was filtered off
  13. customcrystallized from methanol

Sources & evidence

ORD record
ord-26cdd1d813fc46d1a55367b749a45836
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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