Mesitylene → 3-Allyl-5-ethoxy-4-hydroxybenzaldehyde

HRID 746331Notes

Reaction equation

HRID 746331 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12]CC=C)[CH:7]=[O:8])[CH3:2].[OH-].[Na+].[C:18]1(C)[CH:23]=C(C)C=C(C)[CH:19]=1>>[CH2:23]([C:10]1[CH:9]=[C:6]([CH:5]=[C:4]([O:3][CH2:1][CH3:2])[C:11]=1[OH:12])[CH:7]=[O:8])[CH:18]=[CH2:19]

Participants

4

Reactant 3

HCID 7947MesityleneHCID 14798Sodium HydroxideHCID 35257364-(allyloxy)-3-ethoxybenzaldehyde

Product 1

HCID 8813293-Allyl-5-ethoxy-4-hydroxybenzaldehyde

Procedure

3-Ethoxy-4-(2-propenyloxy)benzaldehyde (20.0 g, 0.087 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 a light orange-colored 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, there
  6. customthat crystallized
  7. temperatureon cooling

Sources & evidence

ORD record
ord-9228b63a0d4f4087b9617c6b7a5a7776
Source dataset
uspto-grants-2008_07
Patent number
US07393367B2

Reaction notes

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