Acetic Anhydride → 3-Allyl-4-acetoxy-cinnamic acid

HRID 597650Notes

Reaction equation

HRID 597650 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[OH:15])[CH:7]=[CH:8][C:9]([OH:11])=[O:10])[CH:2]=[CH2:3].[C:16](OC(=O)C)(=[O:18])[CH3:17]>[OH-].[Na+]>[CH2:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[O:15][C:16](=[O:18])[CH3:17])[CH:7]=[CH:8][C:9]([OH:11])=[O:10])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 540628753-Allyl-4-hydroxy-cinnamic acid

Product 1

HCID 538871623-Allyl-4-acetoxy-cinnamic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

118 g (0.058 mol) of 3-allyl-4-hydroxy-cinnamic acid are dissolved in 580 ml of 2 N sodium hydroxide solution, 800 g of ice are added and 120 g (1.16 mols) of acetic anhydride are introduced dropwise over the course of 15 minutes at 0°-5°C, whilst stirring. The crystals which have precipitated are then separated off, suction-dried and recrystallised from ethyl acetate. 3-Allyl-4-acetoxy-cinnamic acid of melting point 143°-144°C is thus obtained.

Workup

  1. customThe crystals which have precipitated
  2. customare then separated off
  3. customsuction-dried
  4. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-0bfefdbb0fd44876abb7c41d6595340e
Source dataset
uspto-grants-1977_03
Patent number
US04014920

Reaction notes

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