Ethanol → HCID 21544827, compound

HRID 1606793Notes

Reaction equation

HRID 1606793 reaction equation
[C:1]([C:4]1[C:21]([OH:22])=[CH:20][CH:19]=[CH:18][C:5]=1[O:6][CH2:7][CH:8]([OH:17])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:3])[CH3:2].[O-:23][CH2:24][CH3:25].[Na+].[Na].C([OH:30])C>C(OCC)(=O)C(OCC)=O.C1C=CC=CC=1.CCOCC>[C:24]([C:25]1[O:22][C:21]2[C:4]([C:1](=[O:3])[CH:2]=1)=[C:5]([O:6][CH2:7][CH:8]([OH:17])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:18]=[CH:19][CH:20]=2)([OH:30])=[O:23]

Participants

8

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21544797HCID 21544797, compound

Product 1

HCID 21544827HCID 21544827, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolventHCID 7268Diethyl OxalateSolvent

Procedure

A solution of 1-(2-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-phenoxypropane (12.08 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 benzene (100 ml). The mixture was heated under reflux for 1.5 hours, cooled and poured into ether. The precipitated yellow solid was collected, washed with ether and dried. The solid was then added to a mixture of glacial acetic acid (80 ml) and concentrated hydrochloric acid (30 ml) and heated under reflux for 1 hour. After cooling, the reaction mixture was poured with stirring into cold water (1 L). The precipitated gum was washed with water by decantation and solidified by trituration with acetic acid. Recrystallization from acetic acid gave 1-(2-carboxychromon-5-yloxy)-2-hydroxy-3-phenoxypropane (7.0 g) as a white powder, m.p. 88°-90° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperaturecooled
  4. customThe precipitated yellow solid was collected
  5. washwashed with ether
  6. customdried
  7. additionThe solid was then added to a mixture of glacial acetic acid (80 ml) and concentrated hydrochloric acid (30 ml)
  8. temperatureheated
  9. temperatureunder reflux for 1 hour
  10. temperatureAfter cooling
  11. additionthe reaction mixture was poured
  12. washThe precipitated gum was washed with water by decantation
  13. customRecrystallization from acetic acid

Sources & evidence

ORD record
ord-060a4ae06dd04aba8035bbcf9683f65f
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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