Sulfuric Acid → HCID 20537163, compound

HRID 1156175Notes

Reaction equation

HRID 1156175 reaction equation
C(O[C:4](=[O:15])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)C.CC[O-].[Na+].[Na].C(OCC)(=O)[C:22]([O:24]CC)=[O:23].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.C(O)C>[O:15]=[C:4]([CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:22]([OH:24])=[O:23]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 7268Diethyl OxalateHCID 234289ethyl 5-phenylpentanoateHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 20537163HCID 20537163, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

47.9 g of 5-phenylvaleric acid ethyl ester are added to a sodium ethylate suspension, prepared from 6.4 g of sodium and 100 ml of ethanol with subsequent evaporation of excess ethanol and addition of 100 ml of toluene. 44.1 g of diethyl oxalate are added dropwise, whilst stirring, and the mixture is heated under reflux for 2.5 hours. After cooling, the solution is stirred with 500 ml of ice-water and the mixture is acidified to pH 2 with 2 N sulphuric acid. Extraction several times with methylene chloride gives, after drying, filtration through a short silica gel column and concentration, 62.1 g of 3-ethoxycarbonyl-2-oxo-6-phenylhexanoic acid ethyl ester, which is reacted according to (a), without further purification.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2.5 hours
  3. temperatureAfter cooling
  4. extractionExtraction several times with methylene chloride
  5. customgives
  6. customafter drying
  7. filtrationfiltration
  8. concentrationthrough a short silica gel column and concentration, 62.1 g of 3-ethoxycarbonyl-2-oxo-6-phenylhexanoic acid ethyl ester, which
  9. customis reacted
  10. customaccording to (a), without further purification

Sources & evidence

ORD record
ord-336bfdd59cc6404d992bf0e3f350324d
Source dataset
uspto-grants-1982_06
Patent number
US04334089

Reaction notes

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