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2-Ethylhexyl methacrylate → 3-Ethoxy-4-hydroxymandelic acid

HRID 268693
Notes
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Reaction equation

HRID 268693 reaction equation
C/C(/C)=[C:3](/[O:9]C)\[O:4][Si](C)(C)C.[C:12](O[Si](C)(C)C)(=[O:16])[C:13](C)=C.C(OCC(CC)CCCC)(=O)C(C)=C.C[O:37][C:38]1[CH:45]=[CH:44][C:41]([CH:42]=[O:43])=[CH:40][CH:39]=1>ClC1C=CC=CC=1.C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C.C1COCC1.CO>[CH3:13][CH2:12][O:16][C:39]1[CH:40]=[C:41]([CH:42]([OH:43])[C:3]([OH:4])=[O:9])[CH:44]=[CH:45][C:38]=1[OH:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 127132-Ethylhexyl methacrylate2×HCID 312444-MethoxybenzaldehydeHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 27338392-Propenoic acid, 2-methyl-, trimethylsilyl ester

Product 1

HCID 1937923-Ethoxy-4-hydroxymandelic acid

Reagents, catalysts & solvents 4

HCID 68463681
Tetrabutylammonium m-chlorobenzene
Catalyst
HCID 887MethanolSolvent
HCID 6342AcetonitrileSolvent
HCID 8028TetrahydrofuranSolvent3×

Procedure

7 ml of THF and 16 ml of dimethylketene methyltrimethylsilylacetal as an initiator were mixed under an argon gas atmosphere, and stirred for 30 minutes. 0.64 g of tetrabutylammonium m-chlorobenzene catalyst dissolved in 1 ml of acetonitrile was added, and the mixture was stirred for 2 hours. 53.1 ml of trimethylsilyl methacrylate and 4.9 ml of 2-ethylhexyl methacrylate dissolved in 10 ml of THF were added in droplets. After performing the reaction for 2 hours, 9.8 ml of 2-ethylhexyl methacrylate dissolved in 5 ml of THF was added slowly. After performing the reaction for 3 hours, 7.6 g of 4-methoxybenzaldehyde were added to substitute the terminal end of the hydrophobic moiety. After stirring for 12 hours, 120 ml of methanol was added, heated to reflux for 6 hours, and then the solvent was removed under reduced pressures. The resulting solid was dried in a vacuum oven for 24 hours to obtain light yellow EHMA/MAA//EHMA-4-methoxylphenyl block copolymer powders.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 2 hours
  3. additionwere added in droplets
  4. customthe reaction for 2 hours
  5. additionwas added slowly
  6. customthe reaction for 3 hours
  7. stirringAfter stirring for 12 hours
  8. temperatureheated
  9. temperatureto reflux for 6 hours
  10. customthe solvent was removed under reduced pressures
  11. customThe resulting solid was dried in a vacuum oven for 24 hours

Sources & evidence

ORD record
ord-36417995d64a421fbf062cb338ae4f28
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07446135B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes