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

HRID 411664
Notes
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Reaction equation

HRID 411664 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 102366469-Methoxy-7,13-dioxa-dibenzo[a,h]fluoren-12-oneHCID 67725173Pyr-HCl

Product 1

HCID 102863239-Hydroxy-7,13-dioxa-dibenzo[a,h]fluoren-12-oneYield 59.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

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

  1. filtrationfiltered
  2. customThe precipitate thus obtained
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes