4-Hydroxybenzaldehyde → p-(Octyloxy)benzaldehyde

HRID 1484084Notes

Reaction equation

HRID 1484084 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>>[CH2:11]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 81401-BromooctaneHCID 10796Cesium carbonate

Product 1

HCID 90358p-(Octyloxy)benzaldehydeYield 95.1%

Conditions

Temperature
80 °C

Procedure

4-hydroxybenzaldehyde (8.2 mmols), 1-bromooctane (12.3 mmols) and cesium carbonate (16.4 mmols) were dissolved in DMF (13.7 mmols). The mixture was then heated to 80° C. and stirred for 3 hours. After this time, the reaction mixture was filtered through a fine fritted funnel; the eluent was collected and diluted with 200 mLs of EtOAc. The organic layer was extracted with seven 10 mL portions of H2O and two 15 mL portions of brine. The organic layer was dried with MgSO4 and evaporated to dryness. After purification by flash chromatography 7.8 mmols of the title product was recovered. 1H NMR (500 MHz, CDCl3) δ 9.86 (d, J=2.9, 1H), 7.94-7.74 (m, 2H), 7.05-6.92 (m, 2H), 4.02 (td, J=3.1, 6.5, 2H), 1.88-1.73 (m, 2H), 1.44 (dd, J=6.8, 14.2, 2H), 1.39-1.21 (m, 8H), 0.99-0.81 (m, 3H). 13C NMR (126 MHz, CDCl3) δ 190.76, 164.24, 131.95, 129.70, 114.71, 68.40, 31.77, 29.28, 29.03, 25.95, 22.63, 14.08.

Workup

  1. filtrationAfter this time, the reaction mixture was filtered through a fine fritted funnel
  2. customthe eluent was collected
  3. additiondiluted with 200 mLs of EtOAc
  4. extractionThe organic layer was extracted with seven 10 mL portions of H2O and two 15 mL portions of brine
  5. dry with materialThe organic layer was dried with MgSO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-0f8d3bc7b0ea4ea288f37684ed017ff1
Source dataset
uspto-grants-2016_08
Patent number
US09421177B2

Reaction notes

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