Sulfuric Acid → HCID 23125842, compound

HRID 132729Notes

Reaction equation

[OH:1][CH2:2][C:3]1([CH2:16][OH:17])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2.[C:18]([OH:22])(=O)[CH:19]=[CH2:20].[C:23]1([CH3:29])C=CC=C[CH:24]=1.S(=O)(=O)(O)[OH:31]>O>[C:29]([O:1][CH2:2][C:3]1([CH2:16][O:17][C:18](=[O:22])[CH:19]=[CH2:20])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)(=[O:31])[CH:23]=[CH2:24]

Participants

Conditions

Temperature: 70 °C

Procedure

To 6.8 g (0.03 mol) 9,9-di(hydroxymethyl)fluorene was added 4.3 ml (0.06 mol) acrylic acid and 30 ml toluene. To the resulting homogenous mixture was added 0.2 ml concentrated sulfuric acid. Then the reaction mixture was heated refluxing for 7 hours, and the water resulted in the reaction process was separated by a water separator. The mixture was cooled to 70° C., neutralized to alkalinity with saturated sodium carbonate solution, and extracted with toluene. The organic phase was washed with saturated saline to neutrality and dried over anhydrous sodium sulfate. The solvent was removed. Purification by column chromatography gave 9,9-bis(acryloyloxymethyl)fluorene as a white solid, and the yield was 35%. m.p. was 73-75° C. 1HNMR: δ (ppm) 4.48(s, 4H, OCH3), 5.85-6.43(m, 6H, H on acryl), 7.32-7.78(m, 8H, ArH)

Workup

temperatureThen the reaction mixture was heated
temperaturerefluxing for 7 hours
customwas separated by a water separator
extractionextracted with toluene
washThe organic phase was washed with saturated saline to neutrality
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed
customPurification by column chromatography

Sources & evidence

ORD record: ord-6624b75723ae49048122574af9c42322
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07388061B2

Reaction notes

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