Acetone → HCID 23371776, compound

HRID 1899861Notes

Reaction equation

HRID 1899861 reaction equation
[Br:1][C:2]1[C:3](O)=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6](C)[CH:7]=1.[CH3:13][C:14]([CH3:16])=[O:15].N1CCC[CH2:18]1.O>C1C=CC=CC=1>[Br:1][C:2]1[C:7]([CH3:18])=[CH:6][C:5]2[O:15][C:14]([CH3:16])([CH3:13])[CH2:10][C:9](=[O:11])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 31268PyrrolidineHCID 111389181-(3-Bromo-2-hydroxy-5-methylphenyl)ethan-1-one

Product 1

HCID 23371776HCID 23371776, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of the product of step b (48 g), acetone (31 ml) and pyrrolidine (21 ml) in dry benzene (500 ml) is stirred at room temperature for 3 h and then at reflux for 6 h with water formed being removed via a Dean-Stark apparatus. The cooled mixture is treated with HCl (200 ml, 2M), stirred for 10 min, basified with aqueous NaOH (1M) and extracted with CH2Cl2 (3×300 ml). The combined extracts are dried (K2CO3), filtered and the solvent is evaporated off under reduced pressure to yield the crude product. This is purified by chromatography (silica gel, 50% toluene in hexane) and recrystallized from diethyl ether-pentane to give the title compound, m.p. 95°-96° C.

Workup

  1. customformed
  2. custombeing removed via a Dean-Stark apparatus
  3. additionThe cooled mixture is treated with HCl (200 ml, 2M)
  4. stirringstirred for 10 min
  5. extractionextracted with CH2Cl2 (3×300 ml)
  6. dry with materialThe combined extracts are dried (K2CO3)
  7. filtrationfiltered
  8. customthe solvent is evaporated off under reduced pressure
  9. customto yield the crude product
  10. customThis is purified by chromatography (silica gel, 50% toluene in hexane)
  11. customrecrystallized from diethyl ether-pentane

Sources & evidence

ORD record
ord-f8504788876a40ee808ff6e470d1002b
Source dataset
uspto-grants-1996_11
Patent number
US05574049

Reaction notes

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