Methyl Ethyl Ketone → HCID 21474593, compound

HRID 2256352Notes

Reaction equation

HRID 2256352 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[C:7](=O)[CH2:6][CH:5]=[CH:4][C:3]1=2.[OH:16][C:17]1[CH:26]=[C:25]([OH:27])[CH:24]=[C:23]([OH:28])[C:18]=1[C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[K+].[K+].[CH2:35]([C:37](C)=[O:38])C>>[OH:16][C:17]1[CH:26]=[C:25]([O:27][CH2:35][C:37]([C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:15])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=3[CH:7]=2)=[O:38])[CH:24]=[C:23]([OH:28])[C:18]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 76600Benzoic acid, 2,4,6-trihydroxy-, methyl esterHCID 86751137HCID 86751137, compound

Product 1

HCID 21474593HCID 21474593, compound

Procedure

3.1 g (10 mmol) of 2-(2'-bromoaceto)-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthone, 1.8 g (10 mmol) of methyl 2,4,6-trihydroxybenzoate, 1.4 g (10 mmol) of potassium carbonate and 100 ml of methyl ethyl ketone are introduced into a flask. The mixture is heated under reflux for 1 hour and evaporated to dryness. The residue is taken up with water and dichloromethane, and the organic phase is separated, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column, eluted with a mixture of dichloromethane and hexane (50:50). After evaporation of the solvents, 2.2 g (53%) of the expected product of melting point 169°-170° C. are collected.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 1 hour
  3. customevaporated to dryness
  4. customthe organic phase is separated
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a silica column
  9. washeluted with a mixture of dichloromethane and hexane (50:50)
  10. customAfter evaporation of the solvents, 2.2 g (53%) of the expected product of melting point 169°-170° C.
  11. customare collected

Sources & evidence

ORD record
ord-e03fe56085384b3080410b0f969b8328
Source dataset
uspto-grants-1997_08
Patent number
US05654331

Reaction notes

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