4-Hydroxybenzaldehyde → 1,10-di(4-formylphenoxy)decane

HRID 335351Notes

Reaction equation

HRID 335351 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][CH2:18][CH2:19][CH2:20]Br.[OH-:22].[K+]>CN(C=O)C>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:22][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 14797Potassium HydroxideHCID 2214831,10-Dibromodecane

Product 1

HCID 40309311,10-di(4-formylphenoxy)decane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

24.4 g (0.2 mol) of p-hydroxybenzaldehyde, 30 g (0.1 mol) of 1,10-dibromodecane and 11.2 g (0.2 mol) of KOH (85%) are heated under reflux in 200 ml of DMF for 30 min. The solution is then allowed to cool to room temperature and is poured into water/ice. The resulting solid is isolated by suction filtration. For purification, the product, which is still moist, is recrystallized from ethanol/water and dried at 70-80° C.

Workup

  1. customThe resulting solid is isolated by suction filtration
  2. customFor purification
  3. customis recrystallized from ethanol/water
  4. customdried at 70-80° C.

Sources & evidence

ORD record
ord-05242933ef024f49868472948bf80e08
Source dataset
uspto-grants-2014_11
Patent number
US08883931B2

Reaction notes

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