4-Hydroxybenzaldehyde → HCID 18925383, compound

HRID 1289167Notes

Reaction equation

HRID 1289167 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH2:11]Br)[CH:8]=[C:7]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:6]=1[O:17][CH3:18])([CH3:4])([CH3:3])[CH3:2].[OH:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:1]([C:5]1[CH:10]=[C:9]([CH2:11][O:19][C:20]2[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=2)[CH:8]=[C:7]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:6]=1[O:17][CH3:18])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 12142455Benzene, 5-(bromomethyl)-1,3-bis(1,1-dimethylethyl)-2-methoxy-

Product 1

HCID 18925383HCID 18925383, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Under a nitrogen atmosphere 1,3-di(t-butyl)-2-methoxy-5-bromomethylbenzene (6.26 g, 20 mmol) is then reacted with 4-hydroxybenzaldehyde (2.44 g, 20 mmol) and potassium carbonate (3.04 g) in 140 ml of methyl ethyl ketone. The reaction mixture is heated to reflux and maintained at this temperature for about 18 hours at which time the reaction mixture is cooled. The inorganics are removed by filtration and the filtrate is concentrated in vacuo. The concentrated reaction products are purified by silica gel chromatography to yield 5.8 grams (81%) of 4-[[3,5-di(t-butyl)-4-methoxyphenyl]methoxy]benzaldehyde.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. temperaturemaintained at this temperature for about 18 hours at which time the reaction mixture
  4. temperatureis cooled
  5. customThe inorganics are removed by filtration
  6. concentrationthe filtrate is concentrated in vacuo
  7. customThe concentrated reaction products
  8. customare purified by silica gel chromatography

Sources & evidence

ORD record
ord-251db71c2c4040fd9add67f50cf930c8
Source dataset
uspto-grants-1998_05
Patent number
US05747517

Reaction notes

Loading…