Hydrochloric Acid → HCID 22769812, compound

HRID 1657687Notes

Reaction equation

HRID 1657687 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:7]([C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[O:14][CH2:15][CH2:16][OH:17])([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C.Cl>O1CCCC1.O>[C:1]([O:17][CH2:16][CH2:15][O:14][C:13]1[CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]([OH:21])=[C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[CH:12]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 22769816HCID 22769816, compound

Product 1

HCID 22769812HCID 22769812, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2-(3,5-ditert.butyl-4-hydroxyphenoxy)ethyl methacrylate was prepared by adding dropwise a solution of 3.1 grams of methacryloyl chloride in 15 milliliters of tetrahydrofuran to a solution of 7 grams of 2-(3,5-ditert.butyl-4-hydroxyphenoxy)ethanol and 11 grams of triethylamine in 50 milliliters of tetrahydrofuran. The addition was completed in 5 minutes and the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was then poured into a solution of 20 milliliters of concentrated hydrochloric acid in 400 milliliters of water and the oil which precipitated was separated by extraction with petroleum ether. The extract was allowed to evaporate and the solid residue was recrystallized from petroleum ether to yield 4 grams of product which melted at 68° C. to 70° C.

Workup

  1. additionThe addition
  2. customthe oil which precipitated
  3. customwas separated by extraction with petroleum ether
  4. customto evaporate
  5. customthe solid residue was recrystallized from petroleum ether

Sources & evidence

ORD record
ord-11fa79ff45514188a17a52c6efa53f1f
Source dataset
uspto-grants-1976_06
Patent number
US03962187

Reaction notes

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