4-Hydroxybenzaldehyde → 4-Hydroxy-alpha-methylcinnamic acid

HRID 359071Notes

Reaction equation

HRID 359071 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([O-:14])(=[O:13])[CH2:11][CH3:12].[Na+].C(OC(=O)CC)(=O)CC>O>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:11]([CH3:12])[C:10]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 31263Propionic anhydrideHCID 2723816Sodium Propionate

Product 1

HCID 2191964-Hydroxy-alpha-methylcinnamic acidYield 75.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-hydroxybenzaldehyde (60 g), sodium propionate (104 g) and propionic anhydride (190 ml) was stirred at 135°-140° C. for 40 hours. After the mixture was allowed to cool, water (600 ml) was added thereto, and stirred under ice cooling for 2-3 hours. The precipitate was collected by filtration, and washed well with water. Sodium hydroxide (60 g) was completely dissolved in water (800 ml) with stirring under ice cooling, and thereto was added the above-mentioned precipitate, and the mixture was stirred at the same temperature for 30 minutes. The insoluble materials were filtered off, and the filtrate was acidified with 5N hydrochloric acid under ice cooling. The resulting precipitate was collected by filtration, washed well with water to give 4-hydroxy-α-methylcinnamic acid (66 g). mp. 204°-205° C.

Workup

  1. temperatureto cool
  2. stirringstirred under ice cooling for 2-3 hours
  3. filtrationThe precipitate was collected by filtration
  4. washwashed well with water
  5. dissolutionSodium hydroxide (60 g) was completely dissolved in water (800 ml)
  6. stirringwith stirring under ice cooling
  7. additionwas added the above-mentioned precipitate
  8. stirringthe mixture was stirred at the same temperature for 30 minutes
  9. filtrationThe insoluble materials were filtered off
  10. filtrationThe resulting precipitate was collected by filtration
  11. washwashed well with water

Sources & evidence

ORD record
ord-7a19f6c3558c43e7b40191d0bfe7dfe2
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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