4-Hydroxybenzaldehyde → HCID 87569461, compound

HRID 1176954Notes

Reaction equation

HRID 1176954 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][C:10]1([CH3:14])[CH2:13][O:12][CH2:11]1.[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:14][C:10]1([CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:15][C:16]2[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=2)[CH2:13][O:12][CH2:11]1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 144346313-{[(6-Bromohexyl)oxy]methyl}-3-methyloxetane

Product 1

HCID 87569461HCID 87569461, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of JYC-I-143-A (5 g, 18.9 mmol), 4-hydroxybenzaldehyde (2.53 g, 20.7 mmol), and K2CO3 (5.21 g, 37.7 mmol) in 50 mL of DMF was heated at 150° C. for 5 h. The reaction mixture was allowed to cool down to room temperature and poured into a separatory funnel containing H2O. The mixture was extracted with CH2Cl2 and the organic phase was washed with H2O and a saturated NaCl aqueous solution. The organic phase was dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give brown oil. The crude product was purified by column chromatography (silica gel, hexanes:ethyl acetate:=4:1 (v/v)) to give light yellow liquid (4.75 g, 82%). 1H NMR (300 MHz, CDCl3, δ): 9.84 (s, 1H), 7.79 (d, J=8.8 Hz, 2H), 6.95 (d, J=8.8 Hz, 2H), 4.47 (d, J=5.5 Hz, 2H), 4.32 (d, J=5.5 Hz, 2H), 4.01 (t, J=6.4 Hz, 2H), 3.45 (t, J=6.4 Hz, 2H), 3.44 (s, 2H), 1.80 (m, 2H), 1.60 (m 2H), 1.44 (m, 4H), 1.27 (s, 3H). 13C{1H} NMR (75 MHz, CDCl3, δ): 190.66, 164.13, 131.88, 129.72, 114.66, 80.09, 76.00, 71.33, 68.20, 39.85, 29.38, 28.94, 25.85, 25.73, 21.30. HRMS-FAB (m/z): [M+H]+ calcd for C18H27O4, 307.1909; found, 307.1905.

Workup

  1. temperatureto cool down to room temperature
  2. additionpoured into a separatory funnel
  3. extractionThe mixture was extracted with CH2Cl2
  4. washthe organic phase was washed with H2O
  5. dry with materialThe organic phase was dried over anhydrous MgSO4
  6. customThe solvent was removed under reduced pressure
  7. customto give brown oil
  8. customThe crude product was purified by column chromatography (silica gel, hexanes:ethyl acetate:=4:1 (v/v))

Sources & evidence

ORD record
ord-99f35e77846b44b891e02730d6e6d293
Source dataset
uspto-grants-2010_11
Patent number
US07842830B2

Reaction notes

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