4-Hydroxybenzaldehyde → HCID 86676461, compound

HRID 1472756Notes

Reaction equation

HRID 1472756 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[O:11][CH2:10][CH2:9][O:8]1.[OH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[O:8]1[CH2:9][CH2:10][O:11][CH:7]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 5520822-(5-bromopentyl)-1,3-dioxolane

Product 1

HCID 86676461HCID 86676461, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 2-(5-bromopentyl)-1,3-dioxolane (4.38 g, 19.6 mmol) in dimethyl formamide (30 mL) was added 4-hydroxybenzaldehyde (3.00 g, 24.4 mmol) and potassium carbonate (4.52 g, 32.8 mmol). The reaction mixture was stirred at 50° C. for 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to afford an oil. The crude material was purified by silica gel column chromatography eluting with 0-100% ethyl acetate in iso-hexane to afford the title compound (1.92 g, 36%).

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. washThe combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution and brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford an oil
  7. customThe crude material was purified by silica gel column chromatography
  8. washeluting with 0-100% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-13b77e9088c2420fbd97e835a3e4e17d
Source dataset
uspto-grants-2015_04
Patent number
US09012644B2

Reaction notes

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