Mesitylene → 3-Bromo-4-hydroxy-5-(prop-2-en-1-yl)benzaldehyde

HRID 746334Notes

Reaction equation

HRID 746334 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10]CC=C)[CH:5]=[O:6].[OH-].[Na+].[C:16]1(C)[CH:21]=C(C)C=C(C)[CH:17]=1>>[CH2:21]([C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([Br:1])[C:9]=1[OH:10])[CH:5]=[O:6])[CH:16]=[CH2:17]

Participants

4

Reactant 3

HCID 7947MesityleneHCID 14798Sodium HydroxideHCID 27166134-(allyloxy)-3-bromobenzaldehyde

Product 1

HCID 597204013-Bromo-4-hydroxy-5-(prop-2-en-1-yl)benzaldehyde

Procedure

3-Bromo-4-(2-propenyloxy)benzaldehyde (20.0 g, 0.083 mol) was heated under reflux in 75 ml mesitylene (1,3,5-trimethylbenzene) for 20 hours. After cooling, 250 ml 2N sodium hydroxide were added to the reaction mixture. The aqueous phase was washed two times with diethyl ether. The aqueous phase was subsequently acidified with concentrated hydrochloric acid under ice cooling and then extracted with ethyl acetate. After drying and concentrating the organic phase, there remained an oil that crystallized on cooling.

Workup

  1. temperatureAfter cooling
  2. washThe aqueous phase was washed two times with diethyl ether
  3. extractionextracted with ethyl acetate
  4. customAfter drying
  5. concentrationconcentrating the organic phase
  6. customcrystallized
  7. temperatureon cooling

Sources & evidence

ORD record
ord-d708f8ab87b842b69c87f4960445db8f
Source dataset
uspto-grants-2008_07
Patent number
US07393367B2

Reaction notes

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