Formic Acid → 4-Pentylbicyclo[2.2.2]octane-1-carboxylic acid

HRID 2309293Notes

Reaction equation

S(=O)(=O)(O)O.Br[C:7]12[CH2:14][CH2:13][C:10]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])([CH2:11][CH2:12]1)[CH2:9][CH2:8]2.[CH:20]([OH:22])=[O:21]>S([O-])([O-])(=O)=O.[Ag+2]>[CH2:15]([C:10]12[CH2:13][CH2:14][C:7]([C:20]([OH:22])=[O:21])([CH2:12][CH2:11]1)[CH2:8][CH2:9]2)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

Conditions

Temperature: 5 °C

Procedure

In another flask, 150 ml of concentrated sulfuric acid and 1.3 g of silver sulfate (Ag2SO4) were mixed and cooled to 5° C., and 5 ml of a solution of 3 g of the aforesaid 1-bromo-4-pentylbicyclo(2,2,2)octane in n--C6H14 was added. Subsequently, 1 ml of 98% HCOOH was gradually added thereto. After the evolution of gas ceased, the reaction solution was added to 600 ml of ice water to deposit crystals. The crystals were collected by filtration to obtain 4-pentylbicyclo[2,2,2]octanecarboxylic acid.

Workup

filtrationThe crystals were collected by filtration

Sources & evidence

ORD record: ord-7cfc741cddf64e0e920c3f0912cde248
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04694098

Reaction notes

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