Water → HCID 178458863, compound

HRID 35784Notes

Reaction equation

HRID 35784 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]([CH3:13])[C:7]=1[CH:14]1[CH2:19][C:18](=[O:20])[C:17]([C:21](=[O:24])[CH2:22][CH3:23])=[C:16]([OH:25])[CH2:15]1.N1C=CC=CC=1.O>ClCCl>[C:1]([O:12][C:10]1[CH:11]=[C:6]([CH3:5])[C:7]([CH:14]2[CH2:15][C:16](=[O:25])[C:17]([C:21](=[O:24])[CH2:22][CH3:23])=[C:18]([OH:20])[CH2:19]2)=[C:8]([CH3:13])[CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 178458861HCID 178458861, compound

Product 1

HCID 178458863HCID 178458863, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Acetyl chloride (0.39 g; 4.9 mmole) in dichloromethane (5 ml) was added to a solution of 5-(2,6-dimethyl-4-hydroxyphenyl)-3-hydroxy-2-propionylcyclohex-2-en-1-one (1.29 g; 4.5 mmole) and pyridine (0.39 g; 4.9 mmole) in dichloromethane (100 ml) at room temperature. The mixture was stirred for 24 hours, then poured into water and extracted with dichloromethane. The organic extract was washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure to give an oily residue. Purification by column chromatography over silica gel (eluant dichloromethane) gave 5-(4-acetyloxy-2,6-dimethylphenyl)-3-hydroxy-2-propionylcyclohex-2-en-1-one (0.63 g; 42.0%) as a pale cream solid.

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customto give an oily residue
  7. customPurification by column chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-9f05f74f86b34655969cca1c21f2c21e
Source dataset
uspto-grants-1988_08
Patent number
US04767879

Reaction notes

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