Methyl Methacrylate → HCID 20480688, compound

HRID 847761Notes

Reaction equation

HRID 847761 reaction equation
[CH:1]1([CH2:7][OH:8])[CH:6]=[CH:5][CH2:4][CH:3]=[CH:2]1.[C:9](OC)(=[O:13])[C:10]([CH3:12])=[CH2:11].C1C2NC3C(=CC=CC=3)SC=2C=CC=1>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[C:9]([O:8][CH2:7][CH:1]1[CH:6]=[CH:5][CH2:4][CH:3]=[CH:2]1)(=[O:13])[C:10]([CH3:12])=[CH2:11]

Participants

5

Reactant 3

HCID 6658Methyl MethacrylateHCID 7108PhenothiazineHCID 2972052,5-Cyclohexadiene-1-methanol

Product 1

HCID 20480688HCID 20480688, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

The method of Example 1 was substantially repeated with 2,5-cyclohexadienylmethanol (40.86 g, 0.37 mol, containing ca. 13% 2-cyclohexenylmethanol), methyl methacrylate (159 mL, 1.5 mol), phenothiazine (0.1 g), and tetraisopropyl titanate (2.0 mL). The excess methyl methacrylate was distilled at 70 mm and the product was distilled to give 57.5 g (87% yield) of clear, colorless liquid 2,5-cyclohexadienylmethyl methacrylate, bp 58° C./0.15 mm to 54° C./0.12 mm. IR (film): ν 3030, 2941, 1709, 1629, 1445, 1309, 1287, 1152, 1009, 979, 934, 873, 810 cm-1. 220 MHz 1H NMR: δ 6.07 (1H, m, methacrylate vinyl), 5.8 (2H, m, vinyl), 5.6 (2H, m, vinyl), 5.50 (1H, m, methacrylate vinyl), 4.04 (2H, d, J=6), 3.1 (1H, m, allylic methine), 2.6 (2H, M, allylic methylene), and 1.93 (3H, m, allylic CH3); the minor impurity of cyclohexenylmethyl methacrylate showed a broad envelope of signals from δ 2.0 to 1.3 and a 6 Hz doublet (--CH2O) at 4.02 which showed it to be 13% of the mixture. 22.63 MHz 13C NMR: δ 167.1, 137.7, 126.3, 125.4, 125.2, 68.0, 35.7, 26.5, 18.3.

Workup

  1. distillationThe excess methyl methacrylate was distilled at 70 mm
  2. distillationthe product was distilled

Sources & evidence

ORD record
ord-23fd9a4c103640f0af7ad9d6e647491e
Source dataset
uspto-grants-1981_10
Patent number
US04293674

Reaction notes

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