Benzene → HCID 21569671, compound

HRID 1579848Notes

Reaction equation

HRID 1579848 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C:4](=[O:7])[CH:3]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15].[CH2:17](O)[CH3:18].S(=O)(=O)(O)O.[CH:25]1C=CC=C[CH:26]=1>>[CH2:25]([O:1][C:2]1[CH2:6][CH2:5][C:4](=[O:7])[C:3]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:26]

Participants

5

Reactant 4

HCID 241BenzeneHCID 702EthanolHCID 1118Sulfuric AcidHCID 10198445HCID 10198445, compound

Product 1

HCID 21569671HCID 21569671, compound

Procedure

A mixture containing 26 parts of 2,5-dioxocyclopentaneheptanoic acid, 560 parts of ethanol, 440 parts of benzene and 14.7 parts of concentrated sulfuric acid is slowly distilled over a period of about 40 hours, during which time approximately 200 parts of distillate is collected. The residual mixture is cooled, diluted with approximately 350 parts of ether, then washed successively with dilute aqueous sodium hydroxide and water. The resulting neutral solution is dried over anhydrous sodium sulfate and evaporated by dryness under reduced pressure to afford, as a yellow liquid, ethyl 2-ethoxy-5-oxocyclopent-1-eneheptanoate, which substance is characterized by an ultraviolet absorption maximum at about 253.5 millimicrons.

Workup

  1. distillationis slowly distilled over a period of about 40 hours, during which time approximately 200 parts of distillate
  2. customis collected
  3. temperatureThe residual mixture is cooled
  4. additiondiluted with approximately 350 parts of ether
  5. washwashed successively with dilute aqueous sodium hydroxide and water
  6. dry with materialThe resulting neutral solution is dried over anhydrous sodium sulfate
  7. customevaporated by dryness under reduced pressure

Sources & evidence

ORD record
ord-bbd03728d36c45de8451c074ea193d8e
Source dataset
uspto-grants-1976_01
Patent number
US03931411

Reaction notes

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