2,6-Di-tert-butyl-4-methylphenol → HCID 21846855, compound

HRID 2256386Notes

Reaction equation

HRID 2256386 reaction equation
[OH-].[CH2:2]([N+:6]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH2:4][CH3:5].[C:19]([C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]=1[OH:34])([CH3:22])([CH3:21])[CH3:20]>C1CCCCC1>[C:19]([C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]=1[O-:34])([CH3:22])([CH3:21])[CH3:20].[CH2:15]([N+:6]([CH2:2][CH2:3][CH2:4][CH3:5])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 21846855HCID 21846855, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
50 °C

Procedure

A 1 liter glass reaction vessel, fitted with a magnetic stirrer, a hose connector, and a septum was purged with nitrogen. Operating in an atmosphere of nitrogen, the vessel was charged with a cyclohexane solution (500 ml) which contained 50 grams poly(isobutylene-co-para-bromomethylstyrene) (Mv=10k, 4.6% para-bromomethylstyrene). A cyclohexane solution of tetrabutylammonium 2,6-di(t-butyl)-4-methylphenoxide was prepared in a second flask under nitrogen by placing 100 ml cyclohexane, 30 ml tetrabutylammonium hydroxide (1M in methanol) and 6.6 g 2,6-di(t-butyl)-4-methylphenol into the flask and concentrating this solution down to half its volume. This solution was then added to the flask containing the poly(isobutylene-co-para-bromomethylstyrene). Then 2.5 ml methacrylic acid was added to the polymer solution and the temperature of the solution was raised to 50° C. The reaction was complete in one hour and the polymer was isolated by precipitation in isopropanol. The polymer was dried in a vacuum oven at 1 mm Hg and 40° C. GPC of the recovered polymer (50 g, 100% yield) was identical to that of the starting poly(isobutylene-co-para-bromomethylstyrene). The analysis for the methacrylate content (FTIR and NMR) indicate that the modified polymer had 0.58 meq/gram which is consistent with the complete conversion of methacrylic acid to methacrylic ester.

Workup

  1. customfitted with a magnetic stirrer
  2. customa hose connector, and a septum was purged with nitrogen
  3. additionOperating in an atmosphere of nitrogen, the vessel was charged with a cyclohexane solution (500 ml) which
  4. concentrationconcentrating this solution down to half its volume
  5. additionThis solution was then added to the flask
  6. additioncontaining the poly(isobutylene-co-para-bromomethylstyrene)
  7. additionThen 2.5 ml methacrylic acid was added to the polymer solution
  8. customthe polymer was isolated by precipitation in isopropanol
  9. customThe polymer was dried in a vacuum oven at 1 mm Hg and 40° C

Sources & evidence

ORD record
ord-ea60a5b185a0469ea3ca69c886f5cfb0
Source dataset
uspto-grants-1997_08
Patent number
US05654379

Reaction notes

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