Benzaldehyde → HCID 53881835, compound

HRID 1276548Notes

Reaction equation

HRID 1276548 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCC([O:13][C:14](=[O:17])[CH2:15][Cl:16])=O>C(Cl)(Cl)(Cl)Cl>[Cl:16][CH2:15][C:14]([O:8][CH:1]([O:17][C:14](=[O:13])[CH2:15][Cl:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:13]

Participants

4

Reactant 2

HCID 240Benzaldehyde2×HCID 10946Chloroacetic anhydride

Product 1

HCID 53881835HCID 53881835, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
35 °C

Procedure

Benzaldehyde (10.0 g, 0.094 mol) and chloroacetic acid anhydride (16.1 g, 0.094 mol) were dissolved in carbontetrachloride (50 ml) under N2 atmosphere. Nafion NR 50 (240 mg) was added and the reaction mixture stirred at 35° C. over night. An additional amount of benzaldehyde (5.0 g) and catalyst (120 mg) was added and the reaction continued for several days. The catalyst was filtered off and the filtrate evaporated. The residue was distilled under reduced pressure (B.p. 123-125° C./0.1 mbar) giving a slightly yellow oil, which solidified upon standing. The yield was 7.9 g, 30% of the theoretical. 1H NMR (CDCl3), d (ppm) rel. to TMS: 7.75 (s, 1H, CH(OCO--)2), 7.57-7.41 (m, 2+3H, Ar-H) and 4.14 (d, 4H CH2Cl).

Workup

  1. waitthe reaction continued for several days
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate evaporated
  4. distillationThe residue was distilled under reduced pressure (B.p. 123-125° C./0.1 mbar)
  5. customgiving a slightly yellow oil, which

Sources & evidence

ORD record
ord-507e1afc8de64bc382df80546e0a4956
Source dataset
uspto-grants-2000_12
Patent number
US06166074

Reaction notes

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