Hydrochloric Acid → 2-(4-Allyloxybutyloxy)fluorene-7-carboxylic acid

HRID 130274

Reaction equation

[C:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH:24]=[CH2:25])=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)(=[O:3])C.Br[O-].[Na+].[OH-].[Na+].BrBr.S([O-])([O-])(=[O:35])=S.[Na+].[Na+].Cl>O.O1CCOCC1>[CH2:23]([O:22][CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:10]1[CH:9]=[CH:8][C:13]2[C:14]3[C:6](=[CH:5][C:4]([C:1]([OH:35])=[O:3])=[CH:16][CH:15]=3)[CH2:7][C:12]=2[CH:11]=1)[CH:24]=[CH2:25]

Participants

Conditions

Temperature: 40 °C

Procedure

A dioxane (380 ml) solution of 2-acetyl-7-(4-allyloxybutyloxy)fluorene 22 g was cooled to 8° C. Sodium hypobromite prepared from water 209 ml, sodium hydroxide 42.7 g and bromine 15.2 ml was dropwise added thereto, and after finishing dropwise adding, the solution was stirred at 40° C. for 15 minutes. The reaction mixture was cooled to 10° C., and then a saturated sodium thiosulfate aqueous solution was added thereto. A solid matter deposited by acidifying the solution with hydrochloric acid was filtered and then dried. The solid matter was recrystallized from acetic acid to obtain 15 g of 2-(4-allyloxybutyloxy)fluorene-7-carboxylic acid. Phase transition temperature: C164N222I.

Workup

additionwas dropwise added
additionafter finishing dropwise adding
temperatureThe reaction mixture was cooled to 10° C.
filtrationwas filtered
customdried
customThe solid matter was recrystallized from acetic acid

Sources & evidence

ORD record: ord-67b74d1e3ba74f68a853bd1f9deaec5b
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07381350B2

Linked notes

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