Carbon Dioxide → HCID 67957414, compound

HRID 571557Notes

Reaction equation

HRID 571557 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[CH:31]=[CH:30][C:11]2[C:12]([OH:29])=[CH:13][C:14]3[CH2:15][C:16]4[CH:17]=[C:18]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH:19]=[CH:20][C:21]=4[C:22]=3[C:10]=2[CH:9]=1.[C:32](=[O:34])=[O:33].Cl>CCCCCC.C(OCC)C.C(OCC)(=O)C>[OH:29][C:12]1[C:11]2[CH:30]=[CH:31][C:8]([O:7][CH3:6])=[CH:9][C:10]=2[C:22]2[C:21]3[CH:20]=[CH:19][C:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:17][C:16]=3[CH:15]([C:32]([OH:34])=[O:33])[C:14]=2[CH:13]=1

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 67957704HCID 67957704, compoundHCID 178418339Butyllithium

Product 1

HCID 67957414HCID 67957414, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of n-butyl lithium (n-BuLi) (2.5M, 47.2 mL) in hexane was added into 500 mL two neck flask which contained 10.0 g of the product of Step 4 in diethyl ether (200 mL). The mixture was refluxed for five hours, cooled to room temperature, and poured rapidly onto crushed dry-ice. When the temperature of reaction mixture reached room temperature, ethyl acetate (150 mL) was added and the resulting mixture was acidified by concentrated hydrochloric acid. The organic layer was recovered and dried over sodium sulfate. After removing the solvent, 9.4 g of 5-hydroxy-2-methoxy-9-phenyl-7H-benzo[c]fluorene-7-carboxylic acid was obtained as a white solid. This step was repeated to produce additional product for the next step.

Workup

  1. temperatureThe mixture was refluxed for five hours
  2. additionpoured rapidly
  3. customWhen the temperature of reaction mixture
  4. customreached room temperature
  5. customThe organic layer was recovered
  6. dry with materialdried over sodium sulfate
  7. customAfter removing the solvent

Sources & evidence

ORD record
ord-e3ba19e97b314d9b8083fc93618690b1
Source dataset
uspto-grants-2015_05
Patent number
US09028728B2

Reaction notes

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