Phthalic Anhydride → HCID 10956766, compound
Reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH3:12][C:13]([CH3:21])([CH:16]([OH:20])[CH:17]([CH3:19])[CH3:18])[CH2:14]O>C1(C)C(C)=CC=CC=1>[CH:17]([CH:16]1[C:13]([CH3:21])([CH3:14])[CH2:12][O:6][C:1](=[O:11])[C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4](=[O:5])[O:20]1)([CH3:19])[CH3:18]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 1 °C
Procedure
A solution of 114.82 g (0.10 mole) of phthalic anhydride and 16.31 g (0.11 mole) of 2,2,4-trimethyl-1,3-pentanediol (TMPD) in 250 mL of xylene was heated for 96 hr as described in Examples 1-3. Xylene was removed on a rotary evaporator at 20 torr, at a base temperature of 68° C. The residue (30.0 g) was diluted with 30 mL of methanol and the resulting slurry cooled to 1° C., filtered, and washed with methanol which had been chilled to -20° C. to give 15.9 g (58% yield) of 7-Isopropyl-8,8-dimethyl-8,9-dihydro-7H-6,10-dioxabenzocyclononene-5,11-dione, which was 99.9% pure by vapor phase chromatography (vpc). The methanol washing from recovery of 7-Isopropyl-8,8-dimethyl-8,9-dihydro-7H-6,10-dioxabenzocyclononene-5,11-dione contained, on a methanol-free basis, 16.4% of 7-Isopropyl-8,8-dimethyl-8,9-dihydro-7H-6,10-dioxabenzocyclononene-5,11-dione, while the residue from stripping xylene from the original reaction mixture contained 41.2% of 7-Isopropyl-8,8-dimethyl-8,9-dihydro-7H-6,10-dioxabenzocyclononene-5,11-dione.
Workup
- customXylene was removed on a rotary evaporator at 20 torr, at a base temperature of 68° C
- additionThe residue (30.0 g) was diluted with 30 mL of methanol
- filtrationfiltered
- washwashed with methanol which
- temperaturehad been chilled to -20° C.
Sources & evidence
- ORD record
- ord-8bc0505a916b40f6b6968ced3deb3bcb
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05994564
Reaction notes
Loading…