Methanol → Methyl 4-(4-fluorophenyl)-4-oxobutanoate

HRID 1283395Notes

Reaction equation

HRID 1283395 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:20]O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH2:8][CH2:9][C:10]([O:12][CH3:20])=[O:11])=[O:7])=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1013593-(4-Fluorobenzoyl)propionic acid

Product 1

HCID 5159157Methyl 4-(4-fluorophenyl)-4-oxobutanoate

Procedure

A solution of 3-(p-fluorobenzoyl)propionic acid (58.8 g.) in anhydrous methanol (250 ml.) was treated with concentrated sulphuric acid (3.2 ml.) and the mixture heated at reflux temperature for 10 hours. It was then concentrated to a volume of 100 ml., cooled and diluted with ice-water. The resultant solid was collected and crystallised from ligroin to yield the ester (59.7 g.), m.p. 48°-50°C.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux temperature for 10 hours
  3. concentrationIt was then concentrated to a volume of 100 ml
  4. temperature, cooled
  5. additiondiluted with ice-water
  6. customThe resultant solid was collected
  7. customcrystallised from ligroin

Sources & evidence

ORD record
ord-1d7891123efe4571a45f6824e62b91c6
Source dataset
uspto-grants-1976_08
Patent number
US03975388

Reaction notes

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