Ethanol → HCID 53955217, compound

HRID 1606818Notes

Reaction equation

HRID 1606818 reaction equation
[C:1]([C:4]1[C:25]([OH:26])=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][CH2:7][CH:8]([OH:21])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1)(=[O:3])[CH3:2].[O-:27][CH2:28][CH3:29].[Na+].[Na].[CH2:32]([OH:34])[CH3:33]>C(OCC)(=O)C(OCC)=O.CCOCC>[C:28]([C:29]1[O:26][C:25]2[C:4]([C:1](=[O:3])[CH:2]=1)=[C:5]([O:6][CH2:7][CH:8]([OH:21])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[CH:12]=1)[CH:22]=[CH:23][CH:24]=2)([O:34][CH2:32][CH3:33])=[O:27]

Participants

7

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21544841HCID 21544841, compound

Product 1

HCID 53955217HCID 53955217, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7268Diethyl OxalateSolvent

Procedure

A suspension of 1-(2-acetyl-3-hydroxyphenoxy)-2-hydroxy-3 -(m-trifluoromethylphenoxy) propane (29.6 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 resulting solution was heated under reflux for 2 hours, cooled, and poured onto ice (200 g). After acidification with a solution of acetic acid (24 ml) in water (160 ml), the ether layer was separated, and the aqueous layer extracted with ether (3 × 50 ml). The combined extracts were evaporated under reduced pressure, and the residue dissolved in ethanol (96%, 100 ml) to which hydrochloric acid (20 drops) was added. This solution was heated under reflux for 1 hour, and the ethanol then removed under reduced pressure to give a beige solid, which was crystallized from aqueous ethanol to yield 1-(2-carbethoxychromon-5-yloxy)-2-hydroxy-3-(m-trifluoromethylphenoxy) propane (19.5 g) as white needles m.p. 70°- 75° C.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. additionpoured onto ice (200 g)
  5. customAfter acidification with a solution of acetic acid (24 ml) in water (160 ml), the ether layer was separated
  6. extractionthe aqueous layer extracted with ether (3 × 50 ml)
  7. customThe combined extracts were evaporated under reduced pressure
  8. dissolutionthe residue dissolved in ethanol (96%, 100 ml) to which hydrochloric acid (20 drops)
  9. additionwas added
  10. temperatureThis solution was heated
  11. temperatureunder reflux for 1 hour
  12. customthe ethanol then removed under reduced pressure
  13. customto give a beige solid, which
  14. customwas crystallized from aqueous ethanol

Sources & evidence

ORD record
ord-80733e751920440280ffce13334f7aea
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

Loading…