Benzyl Chloride → HCID 14986292, compound

HRID 1613046Notes

Reaction equation

HRID 1613046 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([CH2:11][CH2:12][CH3:13])[C:5]=1[OH:14].C(Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)(O)[O-].[Na+]>CO.[OH-].[Na+].CN(C)C=O>[C:17]1([CH2:1][O:2][C:3](=[O:15])[C:4]2[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([CH2:11][CH2:12][CH3:13])[C:5]=2[OH:14])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 7503Benzyl ChlorideHCID 516892Sodium BicarbonateHCID 13019281Methyl 2,4-dihydroxy-3-propylbenzoate

Product 1

HCID 14986292HCID 14986292, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 37 g (0.18 mol) of 2,4-dihydroxy-3-propylbenzoic acid methyl ester in 750 mL of methanol and 415 mL of 3N sodium hydroxide was stirred at reflux for 3 hours. The methanol was removed under reduced pressure and the residue was treated with water and 6N hydrochloric acid to acidify. The solid product was extracted with ethyl acetate and the extract was dried and concentrated under reduced pressure to a tan solid which was used without purification. This crude acid (35 g, 0.18 mol), 23 mL (0.2 mol) of benzyl chloride and 17 g (0.2 mol) of sodium bicarbonate in 250 mL of anhydrous dimethylformamide was stirred and heated at 60° for 23 hours. The solvent was removed under reduced pressure and the residue was treated with saturated sodium bicarbonate solution and the product was extracted with ethyl acetate. The dried extract was concentrated under reduced pressure and the residual oil was purified by HPLC using 15% ethyl acetate hexane to give 36 g (70% yield), mp 86°-88° of 2,4-dihydroxy-3-propylbenzoic acid phenylmethyl ester.

Workup

  1. temperatureat reflux for 3 hours
  2. customThe methanol was removed under reduced pressure
  3. additionthe residue was treated with water and 6N hydrochloric acid
  4. extractionThe solid product was extracted with ethyl acetate
  5. customthe extract was dried
  6. concentrationconcentrated under reduced pressure to a tan solid which
  7. customwas used without purification
  8. temperatureheated at 60° for 23 hours
  9. customThe solvent was removed under reduced pressure
  10. additionthe residue was treated with saturated sodium bicarbonate solution
  11. extractionthe product was extracted with ethyl acetate
  12. extractionThe dried extract
  13. concentrationwas concentrated under reduced pressure
  14. customthe residual oil was purified by HPLC

Sources & evidence

ORD record
ord-32f1f2934b1c43539929b13a8fd3d1bb
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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