4-Hydroxybenzyl Alcohol → HCID 22123752, compound

HRID 342815Notes

Reaction equation

HRID 342815 reaction equation
[CH2:1]([C:5](C)=[O:6])[CH:2](C)C.[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1.C(Cl)(=O)C=C>C(N(CC)CC)C>[C:5]([O:14][CH2:13][C:12]1[CH:15]=[CH:16][C:9]([OH:8])=[CH:10][CH:11]=1)(=[O:6])[CH:1]=[CH2:2]

Participants

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 7909Methyl Isobutyl KetoneHCID 13140Acryloyl chloride

Product 1

HCID 22123752HCID 22123752, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1400 g of methyl isobutyl ketone, 50 g of 4-hydroxybenzyl alcohol and 40 g of triethylamine were charged into a separable flask having a capacity of 3 liters, provided with a stirrer and a nitrogen gas feed tube, and deaerated for 30 minutes, and then 33 g of acrylic acid chloride was dropwise added thereto at 3° C. over 50 minutes. Then, stirring was continued at room temperature for 3 hours. After completion of the reaction, the reaction mixture was recovered by filtration. The filtrate was washed with 0. 5N hydrochloric acid and with water, dehydrated over anhydrous sodium sulfate, and then subjected to silica gel column chromatography (eluent: n-hexane/ethyl acetate =10/1 by volume) to obtain the desired fraction. By distilling off the methyl isobutyl ketone solvent from the fraction under reduced pressure, 15 g of 4-hydroxybenzyl acrylate of the following chemical formula was obtained (yield: 26%): ##STR7##

Workup

  1. customprovided with a stirrer and a nitrogen gas feed tube
  2. waitat 3° C. over 50 minutes
  3. waitwas continued at room temperature for 3 hours
  4. customAfter completion of the reaction
  5. filtrationthe reaction mixture was recovered by filtration
  6. washThe filtrate was washed with 0
  7. customto obtain the desired fraction
  8. distillationBy distilling off the methyl isobutyl ketone solvent from the fraction under reduced pressure, 15 g of 4-hydroxybenzyl acrylate of the following chemical formula
  9. customwas obtained (yield: 26%)

Sources & evidence

ORD record
ord-787a53a651174126834691add2e4d003
Source dataset
uspto-grants-1999_01
Patent number
US05859144

Reaction notes

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