HCID 86733275, compound → HCID 21402604, compound

HRID 973265Notes

Reaction equation

HRID 973265 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 2 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-819a490348f54dab9853cdacf3749366
Source dataset
uspto-grants-1977_10
Patent number
US04055654

Reaction notes

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