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Glycidyl methacrylate → 3-Ethoxy-4-hydroxymandelic acid

HRID 2165712
Notes
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Reaction equation

HRID 2165712 reaction equation
C[Si](C)(C)O[C:4]([O:8]C)=[C:5]([CH3:7])[CH3:6].ClC1C=C(C=CC=1)[C:16]([O-:18])=[O:17].C([N+](CCCC)(CCCC)CCCC)CCC.[C:39]([O:44][CH2:45][CH:46]1[O:48][CH2:47]1)(=O)[C:40](C)=C.C(OCC(CC)CCCC)(=O)C(C)=C>C(#N)C.CO.O1CCCC1.C1(C)C(C)=CC=CC=1.O1CCCC1.C1COCC1>[CH3:40][CH2:39][O:44][C:45]1[CH:6]=[C:5]([CH:4]([OH:8])[C:16]([OH:18])=[O:17])[CH:7]=[CH:47][C:46]=1[OH:48]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 7837Glycidyl methacrylate2×HCID 127132-Ethylhexyl methacrylateHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 21922187Tetrabutylammonium m-chlorobenzoate2×

Product 1

HCID 1937923-Ethoxy-4-hydroxymandelic acid

Reagents, catalysts & solvents 5

HCID 887
Methanol
Solvent
3×
HCID 6342AcetonitrileSolvent
HCID 7237O-XyleneSolvent
HCID 8028TetrahydrofuranSolvent
HCID 22180045THF tetrahydrofuraneSolvent

Conditions

Temperature
10 °C

Procedure

A 250 ml round bottom flask, equipped with a mechanical stirrer, thermometer, and nitrogen inlet, is charged with tetrahydrofuran THF (75.6 gm), 1-trimethylsiloxy-1-methoxy-2-methylpropene (7.0 gm, 0.0402M), xylene (1.0 gm), and tetrabutylammonium m-chlorobenzoate (400 μl of a 1.0M solution in acetonitrile). The flask is cooled to 10° C. Feed I consists of tetrahydrofuran (4.0 gm) and tetrabutylammonium m-chlorobenzoate (400 μl of a 1.0M solution). It is added over 50 minutes. Feed II is glycidyl methacrylate (17.3 gm, 0.122M). It is started simultaneously with the start of the feed I. Feed II is added over one minute. Feed III is 2-ethylhexyl methacrylate (40.7 gm, 0.206M). Feed III is started 9 minutes after feed I has begun. Feed III is added over 30 minutes. The temperature of the flask rises to about 41.0° C. After feed I is completed the flask is cooled to 10° C. Feed IV is glycidyl methacrylate (17.1 gm, 0.120M). It is started 8 minutes after feed I is completed. Feed IV is added over 1 minute. At 70 minutes of total reaction time (11 minutes after feed IV is completed) methanol (10.0 gm) is added to the flask.

Workup

  1. customA 250 ml round bottom flask, equipped with a mechanical stirrer
  2. additionIt is added over 50 minutes
  3. customrises to about 41.0° C
  4. temperatureis cooled to 10° C

Sources & evidence

ORD record
ord-a4a00c4dab1444919ec22db641660e9d
Source dataset
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04940761

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes