Chloroacetyl chloride → HCID 592476, compound

HRID 614879Notes

Reaction equation

HRID 614879 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].N1C(C)=CC(C)=CC=1C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>C(Cl)(Cl)Cl>[Cl:21][CH2:22][C:23]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6])=[O:24]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 79532,4,6-TrimethylpyridineHCID 12127Isovanillin

Product 1

HCID 592476HCID 592476, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

A stirred mixture containing 108 g. (710 mmol.) of 3-hydroxy-4-methoxybenzaldehyde, 500 ml. of chloroform, and 125 ml. of collidine was kept below 10° C., treated dropwise with 70 ml. (800 mmol.) of chloroacetyl chloride over a 1-hour period, and then stirred 2 hours at 25° C. The solution was serially extracted with 500-ml. portions of water, 0.3N HCl, and water (2×). Chloroform was evaporated and crude 3-chloroacetoxy-4-methoxybenzaldehyde was recrystallized from diethyl ether (147 g., 91%), m.p. 88°-89° C.

Workup

  1. additionA stirred mixture containing 108 g
  2. customwas kept below 10° C.
  3. additiontreated dropwise with 70 ml
  4. extractionThe solution was serially extracted with 500-ml
  5. customChloroform was evaporated
  6. customcrude 3-chloroacetoxy-4-methoxybenzaldehyde was recrystallized from diethyl ether (147 g., 91%), m.p. 88°-89° C.

Sources & evidence

ORD record
ord-ecff655acb0a4025b592dac89c6b380d
Source dataset
uspto-grants-1979_03
Patent number
US04146650

Reaction notes

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