Acetic Acid → 1-Cyclohexyl-3-(2-hydroxy-3-methylphenyl)-1,3-propanedione

HRID 1200180Notes

Reaction equation

HRID 1200180 reaction equation
C1(C([O:9][C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[C:17](=[O:19])[CH3:18])=O)CCCCC1.[H-].[Na+].O.[C:23]([OH:26])(=O)[CH3:24]>O1CCCC1>[CH:24]1([C:23](=[O:26])[CH2:18][C:17]([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:10]=2[OH:9])=[O:19])[CH2:14][CH2:15][CH2:10][CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 24758Sodium hydrideHCID 146504262-Acetyl-6-methylphenyl cyclohexanecarboxylate

Product 1

HCID 146504291-Cyclohexyl-3-(2-hydroxy-3-methylphenyl)-1,3-propanedione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Acetyl-6-methylphenyl cyclohexanecarboxylate (5.2 g) was dissolved in anhydrous tetrahydrofuran (50 ml) and to the solution was added 60% sodium hydride (880 mg) by portions with stirring at room temperature. After stirring under reflux for 2 hours, the mixture was poured into cold water, acidified with acetic acid and then extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and then concentrated under reduced pressure to obtain the title compound (5.2 g) as crystals in a quantitative yield. The crystals were recrystallized from methanol to obtain the prisms, m.p. 42°-43° C.

Workup

  1. stirringAfter stirring
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dcf0059fd45f4dd299d5b84dd1354bd5
Source dataset
uspto-grants-1990_02
Patent number
US04904690

Reaction notes

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