Sodium Hydroxide → HCID 21163152, compound

HRID 1278272Notes

Reaction equation

HRID 1278272 reaction equation
[OH-].[Na+].[C:3]([C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][CH:12]2[CH2:14][O:13]2)=[C:8]([CH2:17][CH2:18][CH2:19][CH3:20])[C:7]=1[OH:21])(=[O:5])[CH3:4].[OH:22][C:23]1[CH:40]=[CH:39][C:26]2[C:27](=[O:38])[CH:28]=[C:29]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[O:30][C:25]=2[C:24]=1[CH2:41][CH2:42][CH3:43]>C(O)C>[C:3]([C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][CH:12]([OH:13])[CH2:14][O:22][C:23]2[CH:40]=[CH:39][C:26]3[C:27](=[O:38])[CH:28]=[C:29]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[O:30][C:25]=3[C:24]=2[CH2:41][CH2:42][CH3:43])=[C:8]([CH2:17][CH2:18][CH2:19][CH3:20])[C:7]=1[OH:21])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 20443886HCID 20443886, compoundHCID 21163128HCID 21163128, compound

Product 1

HCID 21163152HCID 21163152, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To sodium hydroxide (0.6 g) in ethanol (200 ml) was added (4-acetyl-2-n-butyl-3-hydroxyphenoxy)methyloxiran (6 g) and ethyl 3-(7-hydroxy-4-oxo-8-propyl-4H-1-benzopyran-2-yl)propionate (4.56 g). The mixture was refluxed for 6 hours, evaporated to 1/3 volume and acidified. Extraction with ethyl acetate and subsequent washing with 10% sodium hydroxide solution, and water, and evaporation gave a red oil which was chromatographed on silica with chloroform:ethyl acetate (12:1) mixture to yield a solid. Recrystallisation from ethyl acetate/cyclohexane mixture afforded the title ester as buff micro needles (2.3 g), mp 118°-118.5°.

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. customevaporated to 1/3 volume
  3. extractionExtraction with ethyl acetate
  4. washsubsequent washing with 10% sodium hydroxide solution, and water, and evaporation
  5. customgave a red oil which
  6. customwas chromatographed on silica with chloroform:ethyl acetate (12:1) mixture
  7. customto yield a solid
  8. customRecrystallisation from ethyl acetate/cyclohexane mixture

Sources & evidence

ORD record
ord-b1d56770c52149378ce1c6f72369e2d4
Source dataset
uspto-grants-1981_07
Patent number
US04281008

Reaction notes

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