Dichloromethane → HCID 18939124, compound

HRID 1086380Notes

Reaction equation

HRID 1086380 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14].ClCCl>N1C=CC=CC=1>[C:13]([O:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 89178Benzaldehyde, 4-(2-hydroxyethoxy)-

Product 1

HCID 18939124HCID 18939124, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of the crude 4-(2-hydroxyethoxy)benzaldehyde (30 g, 0.18 mol) and acetic anhydride (40 g, 0.40 mol) was dissolved in 125 mL of dry pyridine and heated at reflux for 3 hr, after which time the reaction mixture was poured onto ca. 200 g of crushed ice. The crude oil was taken up into 150 mL of dichloromethane and washed twice with 5% HCl (2×75 mL) and once with brine (1×75 mL). The organic layer was then dried with sodium sulfate and the solvent was removed under reduced pressure. The crude residue was distilled at 148° C. (1×10-3 mm) to give 12.9 g (25% overall yield) of a slightly cloudy liquid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hr
  3. washwashed twice with 5% HCl (2×75 mL) and once with brine (1×75 mL)
  4. dry with materialThe organic layer was then dried with sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. distillationThe crude residue was distilled at 148° C. (1×10-3 mm)
  7. customto give
  8. custom12.9 g (25% overall yield) of a slightly cloudy liquid

Sources & evidence

ORD record
ord-c7ecb865d58747a880a2e3a4cb8fa905
Source dataset
uspto-grants-1991_07
Patent number
US05029979

Reaction notes

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