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Acrylic Acid → 2-tert-Butyl-6-(3-tert-butyl-2-hydroxy-5-methylbenzyl)-4-methylphenyl acrylate

HRID 638668
Notes
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Reaction equation

HRID 638668 reaction equation
[CH2:1]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:15]=1[OH:25])[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:3]=1[OH:13].[C:26](O)(=[O:29])[CH:27]=[CH2:28].C(N(CC)CC)C.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[C:26]([O:25][C:15]1[C:16]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=1[CH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:3]=1[OH:13])(=[O:29])[CH:27]=[CH2:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6581Acrylic AcidHCID 83982,2'-Methylenebis(4-methyl-6-tert-butylphenol)HCID 8471TriethylamineHCID 24813Phosphorus oxychloride

Product 1

HCID 1090582-tert-Butyl-6-(3-tert-butyl-2-hydroxy-5-methylbenzyl)-4-methylphenyl acrylateYield 95%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

To a 2-liter four-necked flask equipped with a thermometer, stirring apparatus, condenser and dropping funnel were added 340.51 g (1.0 mole) of 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 72.06 g (1.0 mole) of acrylic acid, 500 g of toluene and 209.47 g (2.07 moles) of triethylamine. After replacing the air in the container with nitrogen, 105.8 g (0.69 mole) of phosphorus oxychloride was added dropwise with stirring. After completion of the dropwise addition, the reaction solution was kept at 80° C. for 1 hour. Thereafter, the organic layer was washed with water until it became neutral, and toluene was removed under reduced pressure. The residue was then recrystallized from n-hexane to obtain 374.8 g of a white crystalline 2,2'-methylenebis(6-tert-butyl-4-methylphenol) monoacrylate having a melting point of 132° to 134° C. Yield, 95%.

Workup

  1. customTo a 2-liter four-necked flask equipped with a thermometer
  2. additionwas added dropwise
  3. stirringwith stirring
  4. additionAfter completion of the dropwise addition
  5. washThereafter, the organic layer was washed with water until it
  6. customtoluene was removed under reduced pressure
  7. customThe residue was then recrystallized from n-hexane

Sources & evidence

ORD record
ord-c42c7eff2b384c2caeac41c056c503e4
Source dataset
uspto-grants-1985_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04562281

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes