3,4,5,6-Tetrahydrophthalic anhydride → HCID 67317890, compound

HRID 1012949Notes

Reaction equation

[C:1]1(=[O:11])[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[C:3](=O)[O:2]1.[N+:12]([C:15]1[CH:16]=[C:17]([CH2:21]C(O)=O)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].C([O-])(=O)C.[Na+]>C(O)C>[N+:12]([C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=1)[CH:21]=[C:3]1[C:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=2[C:1](=[O:11])[O:2]1)([O-:14])=[O:13]

Participants

Conditions

Temperature: 80 °C

Procedure

4,5,6,7-Tetrahydro-isobenzofuran-1,3-dione (1) (2.50 g, 16.4 mmol) and 3-nitro phenyl acetic acid (2.72 g, 15.0 mmol) were heated in the presence of sodium acetate (60.0 mg, 0.750 mmol) to 240° C. using a ‘Wood's Alloy’ bath. Once the reaction had reached 240° C. an additional amount of sodium acetate (60.1 mg, 0.750 mmol) was added. The reaction mixture was then heated for a further 45 minutes and then cooled to 80° C. Ethanol (20 ml) was added to the thick gum and the mixture slurried for 30 minutes. The resulting suspension was cooled to ambient temperature and filtered. The solid was further washed with additional cold ethanol (2×5 ml) and dried to afford the desired product as a mixture of geometric isomers. Main peak in LC-MS, (2.48 g) and was taken through crude; m/z (LC-MS, ESP), RT=4.48 mins (no ionization observed).

Workup

customhad reached 240° C.
additionwas added
temperatureThe reaction mixture was then heated for a further 45 minutes
temperatureThe resulting suspension was cooled to ambient temperature
filtrationfiltered
washThe solid was further washed with additional cold ethanol (2×5 ml)
customdried

Sources & evidence

ORD record: ord-d4c664fb50fb4e85a4144adce3b6319a
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981890B2

Reaction notes

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