Hydrochloric Acid → Methyl 5-(2-methylphenyl)-4-oxopentanoate

HRID 1833839

Reaction equation

HRID 1833839 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=[O:13].Cl.[CH3:17]O>C(OCC)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=[O:15])[CH2:10][CH2:11][C:12]([O:14][CH3:17])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 213876245-(2-Methylphenyl)-4-oxopentanoic acid

Product 1

HCID 21387649Methyl 5-(2-methylphenyl)-4-oxopentanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5-(2-Methylphenyl)-4-oxopentanoic acid (prepared as described above; 535 g.) was heated under reflux for 1 hour in methanol (5.5 liters) through which was passed gaseous hydrogen chloride. The flow of hydrogen chloride was then stopped and the solution was heated for a further 2 hours. The solution was then evaporated to give a dark coloured oil which was dissolved in diethyl ether (1500 ml.), washed with water and aqueous sodium bicarbonate solution, dried over sodium sulphate and distilled to give methyl 5-(2-methylphenyl)-4-oxopentanoate (248 g.), in the form of a clear yellow oil, b.p. 170°-200° C./0.7-1.0 mm.Hg.

Workup

  1. temperaturethe solution was heated for a further 2 hours
  2. customThe solution was then evaporated
  3. customto give a dark coloured oil which
  4. washwashed with water and aqueous sodium bicarbonate solution
  5. dry with materialdried over sodium sulphate
  6. distillationdistilled

Sources & evidence

ORD record
ord-00a1217b4f424ba3b9ad2f1cf2cccee6
Source dataset
uspto-grants-1978_01
Patent number
US04067723

Linked notes

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