Methyl Methacrylate → HCID 86738031, compound

HRID 847757Notes

Reaction equation

HRID 847757 reaction equation
[CH2:1]([OH:9])/[CH:2]=[CH:3]/[CH:4]=[CH:5][CH2:6][CH2:7][CH3:8].[C:10](OC)(=[O:14])[C:11]([CH3:13])=[CH2:12].C1C2NC3C(=CC=CC=3)SC=2C=CC=1>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[C:10]([O:9][CH2:1]/[CH:2]=[CH:3]/[CH:4]=[CH:5][CH2:6][CH2:7][CH3:8])(=[O:14])[C:11]([CH3:13])=[CH2:12]

Participants

5

Reactant 3

HCID 6658Methyl Methacrylate2×HCID 7108PhenothiazineHCID 86738032HCID 86738032, compound

Product 1

HCID 86738031HCID 86738031, compound

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

The method of Example 1 was substantially repeated with trans, trans-2,4-octadien-1-ol (50.0 g, 0.40 mol), methyl methacrylate (170 mL, 1.6 mol), phenothiazine (1.0 g) and tetraisopropyl titanate (2.0 mL). After a 2-h reaction time the methyl methacrylate was distilled at 70 mm, and the product, at 73° C./0.25 mm, to give 60.3 g (78%) of clear, colorless liquid trans, trans-2,4-octadienyl methacrylate. IR (film): ν 2985, 1712, 1631, 1449, 1310, 1287, 1149, 985, 962, 935, 811 cm-1. UV (isooctane): λmax 230 nm, ε=33,000. 90 MHz 1H NMR: δ 6.4-5.4 (6H, m, vinyl), 4.6 (2H, d, J=7, OCH2 --), 2.05 (2H, q, J=7, allylic CH2), 1.92 (3H, m, allylic CH3), 1.4 (2H, hextet, J=7, CH3CH2CH2 --), 0.90 (3H, t, J=7, CH3CH2 --). 22.63 MHz 13C NMR: δ 166.9, 136.6, 136.2, 134.8, 129.6, 125.2, 124.3, 65.1, 34.8, 22.4, 18.3, 13.6.

Workup

  1. distillationwas distilled at 70 mm

Sources & evidence

ORD record
ord-6f4e1ed6d8f24c498137349ac2ca93fb
Source dataset
uspto-grants-1981_10
Patent number
US04293674

Reaction notes

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