Hydrochloric Acid → HCID 18690228, compound

HRID 1606572Notes

Reaction equation

HRID 1606572 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:7]([C:11]1[CH:17]=[C:16]([OH:18])[CH:15]=[C:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:12]=1[OH:13])([CH3:10])([CH3:9])[CH3:8].Cl.O>O1CCCC1.C(N(CC)CC)C>[C:1]([O:18][C:16]1[CH:17]=[C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:12]([OH:13])=[C:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:15]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 13528Methacryloyl chlorideHCID 755502,6-Di-tert-butylhydroquinone

Product 1

HCID 18690228HCID 18690228, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

3,5-di tert.butyl-4-hydroxyphenyl methacrylate was prepared by adding drop wise a solution of 5.8 grams of methacryloyl chloride in 25 milliliters of tetrahydrofuran to a solution of 11.1 gram of 2,6-di tert.butyl hydroquinone in 80 milliliters of tetrahydrofuran and 20.2 grams of triethylamine. The addition was completed in 15 minutes and the reaction mixture was stirred at room temperature for 5-1/2 hours. The reaction mixture was then poured into a mixture of 20 milliliters of concentrated hydrochloric acid and 400 milliliters of water, and the solid which precipitated was filtered off, dried, and recrystallized from hexane. There was obtained 10 grams of product which melted at 135° C. to 138° C.

Workup

  1. additionThe addition
  2. customthe solid which precipitated
  3. filtrationwas filtered off
  4. customdried
  5. customrecrystallized from hexane

Sources & evidence

ORD record
ord-60d0e337b1854f42b1e59e31c0c8e359
Source dataset
uspto-grants-1976_04
Patent number
US03953402

Reaction notes

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