Dichloromethane → Chloromethyl benzoate

HRID 1583308Notes

Reaction equation

HRID 1583308 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[CH2:11](Cl)[Cl:12]>CCCCCC>[C:1]([O:9][CH2:11][Cl:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 517055Sodium Benzoate

Product 1

HCID 79257Chloromethyl benzoateYield 12%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

By the procedure of Preparation 10, sodium benzoate (29.97 g, 208 mmol) was converted to crude title product, a thick oil which solidified upon standing at room temperature. TLC of this solid (3:2 hexane:methylene chloride, visualization by UV light) showed two contiguous spots (Rf 0.65, 0.75) and a large baseline spot. The solid was treated with generous amounts of hexane and filtered. TLC of the filtrate showed only less polar products; TLC of the solid only baseline salts. The filtrate was concentrated in vacuo to a yellow oil and chromatographed on silica (3:2 hexane:methylene chloride). Fractions containing the least polar (Rf 0.75) spot were combined and concentrated, affording 4.29 g (25.2 mmol, 12.0%) chloromethyl benzoate as a pale yellow oil: 1H NMR (CDCl3) delta 5.95 (s, 2H), 7.15-7.61 (m, 3H), 7.85-8.18 (m, 2H).

Workup

  1. customupon standing at room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo to a yellow oil
  4. customchromatographed on silica (3:2 hexane:methylene chloride)
  5. additionFractions containing the least polar (Rf 0.75) spot
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c900ecaa0dd2434aa50d6dc489815f58
Source dataset
uspto-grants-1985_11
Patent number
US04551452

Reaction notes

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