Hydrochloric Acid → 4-Cyclopentyloxy-3-hydroxybenzaldehyde

HRID 746424Notes

Reaction equation

HRID 746424 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH:17]1(Br)[CH2:21][CH2:20][CH2:19][CH2:18]1.Cl>CN(C=O)C.O>[CH:17]1([O:10][C:9]2[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=2[OH:1])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8728BromocyclopentaneHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 167261494-Cyclopentyloxy-3-hydroxybenzaldehydeYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 3,4-dihydroxybenzaldehyde (5.0 gm, 0.0362 mol), anhydrous potassium carbonate (6.0 gm, 0.0434 mol) and cyclopentyl bromide (6.5 gm, 0.0434 mol) in dry DMF (50 ml) was heated and stirred at 80° C. for 24 hrs. Reaction mixture was then cooled and diluted with water (500 ml), acidified with 1N HCl and extracted with ethyl acetate (3×100 ml). The ethyl acetate extract was washed 5% sodium bicarbonate and brine and dried over anhydrous sodium sulfate. The dried extract on concentration afforded a residue which was purified by silica gel chromatography using 10% ethyl acetate in petroleum ether as the eluent to provide 5.0 gm of the title product as white solid. mp: 87-89° C.

Workup

  1. temperaturewas heated
  2. customReaction mixture
  3. temperaturewas then cooled
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. extractionThe ethyl acetate extract
  6. washwas washed 5% sodium bicarbonate and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. extractionThe dried extract on concentration
  9. customafforded a residue which
  10. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-4371ba8580f9421dab962a92d0bbb1e4
Source dataset
uspto-grants-2008_07
Patent number
US07393846B2

Reaction notes

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