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

HRID 1285034
Notes
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Reaction equation

HRID 1285034 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 284Formic AcidHCID 1118Sulfuric AcidHCID 125349771-Bromo-4-pentylbicyclo[2.2.2]octane

Product 1

HCID 42414664-Pentylbicyclo[2.2.2]octane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 178418844HCID 178418844, compoundCatalyst

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 solutoin 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

  1. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-694ee359751a42d8914bdb67e16a3149
Source dataset
uspto-grants-1986_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04564694

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes