Acetone → HCID 21958383, compound

HRID 1857562Notes

Reaction equation

HRID 1857562 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:11](=[O:14])([O-])[O-].[K+].[K+].I[CH2:18][CH2:19][CH3:20].[CH3:21][C:22](C)=O>>[CH3:21][CH2:22][CH2:11][O:14][C:8]1[CH:9]=[CH:10][CH:2]=[CH:3][C:4]=1[C:5]([O:7][CH2:18][CH2:19][CH3:20])=[O:6]

Participants

5

Reactant 4

HCID 180AcetoneHCID 74203-Hydroxybenzoic AcidHCID 11430Potassium CarbonateHCID 336431-Iodopropane

Product 1

HCID 21958383HCID 21958383, compound

Procedure

A mixture of 3-hydroxybenzoic acid (10 g, 0.072 mol), potassium carbonate (22.0 g, 0.159 mol) and 1-iodopropane (20.5 ml, 35.7 g, 0.210 mol) in acetone (800 ml) was refluxed for 24 hours. The mixture was filtered, the filtrate was concentrated on the rotary evaporator and the concentrate was partitioned between water and diethyl ether. The aqueous layer was extracted with diethyl ether and the combined extracts were washed with saturated sodium bicarbonate solution and brine and then dried (MgSO4) and concentrated. Flash chromatography on silica gel (elution with 20-50% diethyl ether in n-hexane) gave propyl (3-propyloxy)benzoate. Yield 3.031 g.

Workup

  1. temperaturewas refluxed for 24 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated on the rotary evaporator
  4. customthe concentrate was partitioned between water and diethyl ether
  5. extractionThe aqueous layer was extracted with diethyl ether
  6. washthe combined extracts were washed with saturated sodium bicarbonate solution and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9a60ce7f903041388c1275b4b8f3aba0
Source dataset
uspto-grants-2000_11
Patent number
US06147111

Reaction notes

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