4-Hydroxybenzaldehyde → HCID 14997927, compound

HRID 846249Notes

Reaction equation

HRID 846249 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([CH:12]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:13]Br)[CH3:11].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:10]([CH:12]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:13][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH3:11]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 868042-Ethylhexyl bromide

Product 1

HCID 14997927HCID 14997927, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Hydroxybenzaldehyde (61 g) and 2-ethylhexylbromide (106 g) were added to 150 ml of dimethylformamide containing 138 g of potassium carbonate. The mixture was refluxed overnight and then poured into a volume of cold water and extracted with ethyl acetate. The extract was dried, evaporated and distilled (0.1 millimeter vacuum) to yield 4-[(2-ethylhexyl)oxy]benzaldehyde, boiling point (b.p.) 118°-121° C.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. extractionextracted with ethyl acetate
  3. customThe extract was dried
  4. customevaporated
  5. distillationdistilled (0.1 millimeter vacuum)

Sources & evidence

ORD record
ord-9bdaac872f904a2e95ee8afa47102b1e
Source dataset
uspto-grants-1992_08
Patent number
US05135955

Reaction notes

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