4-Hydroxybenzaldehyde → HCID 86749477, compound

HRID 439660Notes

Reaction equation

HRID 439660 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]Br.[OH:11][C:12]1[CH:19]=[CH:18][C:15](C=O)=[CH:14][CH:13]=1.[C:20](=O)([O-])[O-:21].[K+].[K+].O>CN(C=O)C>[CH:20]([CH:5]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][CH2:3][CH2:2][O:11][C:12]1[CH:19]=[CH:18][CH:15]=[CH:14][CH:13]=1)=[O:21]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 783101,8-Dibromooctane

Product 1

HCID 86749477HCID 86749477, compoundYield 549.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 1,8-dibromooctane (8.0 g, 29.5 mmol), p-hydroxy-benzaldehyde (7.2 g, 59 mmol) and potassium carbonate (8.2 g, 6.0 mmol) in DMF (50 ml) was heated to 55° C. with stirring for 8 h. The cooled solution was poured into water and the precipitate was filtered, washed with water, and dried. Recrystallisation from hot ethanol (200 ml) yielded (15) (7.72 g, 73%), m.p. 89° C.-91° C., (Found C. 74.4, H 7.4 %. C22H26O4 requires C 74.5, H 7.4 %), 1H NMR (250.1 MHz, CDCl3) δ: 1.3-1.9(12H, m, alkyl), 4.02(4H, t, J=7 Hz, CH2O), 6.97 and 7.81 (8H, 2 d, J=11 Hz, aromatic), 9.85 (2H, s, CHO); IR (KBr) vmax /cm-1 1698 s, 1598 s, 1156 s, 834 s. m/z 354 (M, 45), 326 (30), 233 (15), 121 (55), 69 (100).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water
  3. customdried
  4. customRecrystallisation from hot ethanol (200 ml)

Sources & evidence

ORD record
ord-d8ad264ddcad47cda320e00fc8e4f8e7
Source dataset
uspto-grants-1996_05
Patent number
US05514878

Reaction notes

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