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4-Methoxyphenol → 2-(2-(Methacryloyloxy)ethylthio)acetic acid

HRID 523618
Notes
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Reaction equation

HRID 523618 reaction equation
[C:1]([O:6][CH2:7][CH2:8][S:9][CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])(=[O:5])[C:2]([CH3:4])=[CH2:3].COC1C=CC(O)=CC=1.C(Cl)(Cl)Cl.CO.CC(O)=O>FC(F)(F)C(O)=O>[C:1]([O:6][CH2:7][CH2:8][S:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:5])[C:2]([CH3:4])=[CH2:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 149584422-(2-Tert-butoxy-2-oxoethylthio)ethyl methacrylateHCID 21866353chloroform methanol HOAc

Product 1

HCID 149584532-(2-(Methacryloyloxy)ethylthio)acetic acidYield 63.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3 (2 g, 7.7 mmol, 1 eqv.) was slowly dissolved in trifluoroacetic acid (TFA) (10 mL) on ice under nitrogen. A trace amount of hydroquinone monomethyl ether (MEHQ) was added to the reaction mixture to prevent polymerisation. The reaction mixture was allowed to warm to room temperature and the reaction mixture was stirred for 2 hours at 55 C. Completion of the reaction was monitored by TLC(CHCl3/MeOH/HOAc, 9:1:0.1 (v/v), Rf: 0.17). Excess of TFA was removed by evaporation and coevaporation with CH2Cl2 and the residue was purified on a silica gel column (Hex/EtOAc, 4:1 (v/v)). Pure 4 was dried with MgSO4 and filtered through Ø 185 mm whatman filter papers. The filtrate was concentrated in vacuo. 1 g (63% yield) 4 was obtained as a light yellow oil.

Workup

  1. custompolymerisation
  2. customExcess of TFA was removed by evaporation and coevaporation with CH2Cl2
  3. customthe residue was purified on a silica gel column (Hex/EtOAc, 4:1 (v/v))
  4. dry with materialPure 4 was dried with MgSO4
  5. filtrationfiltered through Ø 185 mm whatman
  6. filtrationfilter papers
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2af74332a52e455dbfbe09f3f66c82a3
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09339554B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes