4-Methoxy cinnamic acid → 4-Methoxycinnamic acid chloride

HRID 2309780Notes

Reaction equation

HRID 2309780 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9](O)=[O:10])=[CH:5][CH:4]=1.C(Cl)(=O)C([Cl:17])=O>ClC(Cl)C.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([Cl:17])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 132454-Methoxy cinnamic acidHCID 65578Oxalyl chloride

Product 1

HCID 534017724-Methoxycinnamic acid chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

p-Methoxycinnamic acid (52.7 g=0.45 mole) was slurried under N2 in 500 mL of sieve-dried dichloroethane. Oxalyl chloride (146.0 gm=1.15 moles) was added in one portion followed by three drops of DMF. Complete solution was achieved in 30 minutes. The solution was stirred an additional 2 hours, and then the dichloroethane containing excess oxalyl chloride was removed on a 50° C. rotary evaporator. Fresh dichloroethane was twice added to the residue and removed on the rotary evaporator. The amber oil was used without purification. Yield 90.4 gm.

Workup

  1. customthe dichloroethane containing excess oxalyl chloride was removed on a 50° C.
  2. customrotary evaporator
  3. additionFresh dichloroethane was twice added to the residue
  4. customremoved on the rotary evaporator
  5. customThe amber oil was used without purification

Sources & evidence

ORD record
ord-6d4b23cf6f154cbaa6978fade3d2fe14
Source dataset
uspto-grants-1987_09
Patent number
US04696990

Reaction notes

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