Methyl Methacrylate → HCID 86738033, compound

HRID 847758Notes

Reaction equation

HRID 847758 reaction equation
[CH2:1]([OH:11])/[CH:2]=[CH:3]/[CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:12](OC)(=[O:16])[C:13]([CH3:15])=[CH2:14].C1C2NC3C(=CC=CC=3)SC=2C=CC=1>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[C:12]([O:11][CH2:1]/[CH:2]=[CH:3]/[CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])(=[O:16])[C:13]([CH3:15])=[CH2:14]

Participants

5

Reactant 3

HCID 6658Methyl MethacrylateHCID 7108PhenothiazineHCID 86736648HCID 86736648, compound

Product 1

HCID 86738033HCID 86738033, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

The method of Example 1 was substantially repeated with trans, trans-2,4-decadien-1-ol (50.0 g, 0.32 mol), methyl methacrylate (140 mL, 1.3 mol), phenothiazine (1 g), and tetraisopropyl titanate (2 mL). After a 2-h period the excess methyl methacrylate was removed and the product was distilled to give 46.4 g (65% yield) of clear, colorless liquid trans, trans-2,4-decadienyl methacrylate, bp 96°-97° C./0.2 mm. IR (film): ν 2932, 1712, 1629, 1449, 1309, 1285, 1149, 984, 962, 933, 810 cm-1. UV (isooctane): λmax 230 nm, ε=29,000. 90 MHz 1H NMR: δ 6.4-5.4 (6H, m, vinyl), 4.63 (2H, d, J=7, OCH2), 2.10 (2H, q, J=7, allylic CH2), 1.97 (3H, m allylic CH3), 1.3 (6H, m, 3CH2), and 0.90 (3H, t, J=6, CH3CH2). 22.63 MHz 13C NMR: δ 166.9, 136.5, 134.8, 129.4, 125.2, 124.3, 65.1, 32.7, 31.5, 29.0, 22.6, 18.3, 14.0.

Workup

  1. customAfter a 2-h period the excess methyl methacrylate was removed
  2. distillationthe product was distilled

Sources & evidence

ORD record
ord-91756933c33244a98816efd7681dff4b
Source dataset
uspto-grants-1981_10
Patent number
US04293674

Reaction notes

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