9-Methoxy-7,13-dioxa-dibenzo[a,h]fluoren-12-one → 9-Hydroxy-7,13-dioxa-dibenzo[a,h]fluoren-12-one

HRID 411664Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18](=[O:19])[C:17]3[O:16][C:15]4[C:10](=[CH:11][CH:12]=[C:13]5[CH:23]=[CH:22][CH:21]=[CH:20][C:14]5=4)[C:9]=3[O:8][C:7]=2[CH:24]=1.N1C(=O)CC[C@H]1C(O)=O.Cl>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18](=[O:19])[C:17]3[O:16][C:15]4[C:10](=[CH:11][CH:12]=[C:13]5[CH:23]=[CH:22][CH:21]=[CH:20][C:14]5=4)[C:9]=3[O:8][C:7]=2[CH:24]=1

Participants

Conditions

Temperature: 220 °C

Procedure

A mixture of 40 (0.300 g, 0.95 mmol) and Pyr-HCl (approximately 5 g) was heated at 220° C. for 1 h. H2O (100 mL) was added to the cooled reaction mixture and then the H2O mixture heated and filtered. The precipitate thus obtained was triturated with MeOH and then CH2Cl2 to yield 41 (0.17 g) as a white solid: Mp>300° C.; 1H NMR (DMSO-d6) δ 10.96 (s, 1H), 8.46 (d, 1H, J=7.8 Hz), 8.20-8.14 (m, 2H), 8.06-7.99 (m, 2H), 7.84-7.73 (m, 2H), 7.12 (d, 1H, J=2.1 Hz), 7.03 (dd, 1H, J=8.8 Hz, 2.2 Hz); MS 301 (M−H)−.

Workup

filtrationfiltered
customThe precipitate thus obtained
customwas triturated with MeOH

Sources & evidence

ORD record: ord-7e37d4095d7c4dea86b7b87114bd92e6
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559177B2

Reaction notes

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