Methyl Methacrylate → HCID 20567337, compound

HRID 847760Notes

Reaction equation

HRID 847760 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3]/[CH:4]=[CH:5]/[CH2:6][CH:7]=[CH2:8].[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][CH2:2][CH2:3]/[CH:4]=[CH:5]/[CH2:6][CH:7]=[CH2:8])(=[O:14])[C:11]([CH3:13])=[CH2:12]

Participants

5

Reactant 3

HCID 6658Methyl MethacrylateHCID 7108PhenothiazineHCID 12525557HCID 12525557, compound

Product 1

HCID 20567337HCID 20567337, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

The method of Example 1 was substantially repeated, except that a shorter vigreux head (15 cm) was used, with trans-4,7-octadien-1-ol (18.53 g, 0.146 mol), methyl methacrylate (58.8 g, 0.59 mol), phenothiazine (0.5 g), and tetraisopropyl titanate (1.0 mL). When the head temperature rose to 96° C. (pot 117° C.), the methyl methacrylate was removed at 70 mm and the product was distilled to give 24.8 g (87% yield) of clear, colorless liquid trans-4,7-octadienyl methacrylate, bp 64°-65° C./0.2 mm. IR (film): ν 2950, 1712, 1629, 1445, 1311, 1287, 1156, 964, 933, 907, 810 cm-1. UV (isooctane): end absorption. 220 MHz 1H NMR: δ 6.06 (1H, bs, methacrylate vinyl), 5.76 (1H, m, --HC=CH2), 5.50 (1H, m, methacrylate vinyl), 5.41 (2H, m, --HC=CH--), 5.02-4.92 (2H, m, --HC=CH2), 4.11 (2H, t, J=6, OCH2 --), 2.72 (2H, m, doubly allylic CH2), 2.10 (2H, m, allylic CH2), 1.95 (3H, m, allylic CH3), and 1.73 (2H, pentet, J=6, OCH2CH2CH2). 22.63 MHz 13C NMR: δ 167.2, 137.1, 136.7, 130.2, 128.9, 124.9, 115.0, 64.1, 36.8, 29.1, 28.6, 18.3.

Workup

  1. customrose to 96° C.
  2. custom(pot 117° C.)
  3. customthe methyl methacrylate was removed at 70 mm
  4. distillationthe product was distilled

Sources & evidence

ORD record
ord-82cb04d61b154ccfa082f4af4d7c52a7
Source dataset
uspto-grants-1981_10
Patent number
US04293674

Reaction notes

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