HCID 86733275, compound → HCID 21402604, compound

HRID 1606320Notes

Reaction equation

HRID 1606320 reaction equation
[CH2:1]([C:4]1[C:13]2[O:12][C:11]([C:14]([O:16]CC)=[O:15])=[CH:10][C:9](=[O:19])[C:8]=2[C:7]([O:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:6][CH:5]=1)[CH:2]=[CH2:3].[H][H]>[Pd].C(O)C>[CH3:24][CH:23]([CH3:25])[CH2:22][CH2:21][O:20][C:7]1[C:8]2[C:9](=[O:19])[CH:10]=[C:11]([C:14]([OH:16])=[O:15])[O:12][C:13]=2[C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 86733275HCID 86733275, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21402604HCID 21402604, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 12.05 parts of 8-allyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid, ethyl ester in 225 parts of ethanol was treated with 0.2 parts of 5% palladium/charcoal catalyst and hydrogenated at a pressure of 4 atmospheres. After 30 minutes the hydrogen uptake ceased and the reaction mixture was filtered. The volume of the filtrate was reduced and then water was added. On standing 10.2 parts of 5-(3-methyl-n-butoxy)-8-n-propyl-4-oxo-4H-1-benzopyran-2-carboxylic acid, ethyl ester crystallised as yellow needles, melting point 64.5°-65° C. This material was stirred with a hot aqueous solution of sodium bicarbonate containing some ethanol for two hours. The resulting solution was cooled, washed with diethyl ether and acidified with dilute hydrochloric acid. The yellow precipitate was collected and crystallised from aqueous ethanol to give 7.2 parts of 5-(3-methyl-n-butoxy)-8-n-propyl-4-oxo-4H-1-benzopyran-2-carboxylic acid as yellow needles, melting point 166°-167° C.

Workup

  1. filtrationthe reaction mixture was filtered
  2. additionwater was added
  3. customcrystallised as yellow needles, melting point 64.5°-65° C
  4. temperatureThe resulting solution was cooled
  5. washwashed with diethyl ether
  6. customThe yellow precipitate was collected
  7. customcrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-d75afe0274c3456ab5a892a129ee9d00
Source dataset
uspto-grants-1976_04
Patent number
US03952104

Reaction notes

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