Salicyl Alcohol → HCID 86743331, compound

HRID 1723452Notes

Reaction equation

HRID 1723452 reaction equation
[CH3:1][O-:2].[Na+].[OH:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1CO.Cl[CH2:14][CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CO>[OH:2][CH2:1][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH:16]=[CH:15][CH2:14][O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:6]=1

Participants

5

Reactant 3

HCID 5146Salicyl AlcoholHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 10942334Sodium Methoxide

Product 1

HCID 86743331HCID 86743331, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
40 °C

Procedure

154.3 g (0.8 mol) of 28% sodium methoxide solution in methanol was added to a solution which had been obtained by adding 200 ml of methanol to 99.3 g (0.8 mol) of o-hydroxybenzyl alcohol. The resulting mixture was stirred at a temperature of 40° C. for about 1 hour. 122 g (0.8 mol) of chloromethylstyrene from which polymerization inhibitor had been removed by alkali washing was added dropwise to the mixture. The mixture was stirred under reflux for about 4 hours. The material thus refluxed was allowed to cool to room temperature. The resulting NaCl was filtered out. After the methanol was removed from the filtrate by distillation, the residue was repeatedly and thoroughly washed with hexane until chloromethylstyrene, as raw material, and by-products were completely removed therefrom. 400 ml of chloroform was added thereto for dissolution. The resulting solution was washed with distilled water two or three times. The resulting chloroform phase was separated out. The chloroform phase thus separated was dried by sodium sulfate. The chloroform was then removed by distillation to obtain 123 g of a pale yellow liquid (yield: 64%). This liquid was the desired material. It was confirmed by thin layer chromatography (TLC) using silica gel and gas chromatography (GLC) that this product had a high purity (98% or more).

Workup

  1. customhad been obtained
  2. customhad been removed by alkali washing
  3. additionwas added dropwise to the mixture
  4. stirringThe mixture was stirred
  5. temperatureunder reflux for about 4 hours
  6. temperatureThe material thus refluxed
  7. temperatureto cool to room temperature
  8. filtrationThe resulting NaCl was filtered out
  9. customAfter the methanol was removed from the filtrate by distillation
  10. washthoroughly washed with hexane until chloromethylstyrene, as raw material, and by-products
  11. customwere completely removed
  12. addition400 ml of chloroform was added
  13. dissolutionfor dissolution
  14. washThe resulting solution was washed with distilled water two or three times
  15. customThe resulting chloroform phase was separated out
  16. customThe chloroform phase thus separated
  17. dry with materialwas dried by sodium sulfate
  18. customThe chloroform was then removed by distillation

Sources & evidence

ORD record
ord-c0ea71985aae42729af925acfa195767
Source dataset
uspto-grants-1989_08
Patent number
US04861852

Reaction notes

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