Sulfuric Acid → HCID 54558366, compound

HRID 1731560Notes

Reaction equation

OS(O)(=O)=O.[OH:6][CH2:7][CH:8]1[CH:13]2[CH2:14][CH:10]([CH2:11][CH2:12]2)[CH:9]1[CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21].C([O-])(O)=[O:25].[Na+]>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6].O.CC(O)C>[C:7]([CH:8]1[CH:13]2[CH2:14][CH:10]([CH2:11][CH2:12]2)[CH:9]1[CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])([OH:25])=[O:6]

Participants

Conditions

Temperature: -20 °C

Procedure

14.5 ml of Jones solution (26.7 g of chromium trioxide and 23 ml of concentrated H2SO4 made up to 100 ml with water) are allowed to run into a solution of 1.2 g (5 mmol) of methyl 6-(3-hydroxymethyl-bicyclo[2.2.1]hept-2-yl)-hex-5-enoate in 250 ml of absolute acetone at -20° C. The mixture is stirred at -20° C. for 3 hours and 40 ml of 2-propanol, followed by 30 ml of water, are then added and the pH is brought to 4 with solid NaHCO3. The precipitate is decanted off, the solution is evaporated in vacuo and the residue is extracted 3 times with ethyl acetate. After the ethyl acetate phase has been dried over sodium sulphate, it is evaporated in vacuo and the methyl 6-(3-carboxybicyclo[2.2.1]hept-2-yl)-hex-5-enoate is purified as described under (a). 1.0 g (yield: 75%).

Workup

additionare then added
customThe precipitate is decanted off
customthe solution is evaporated in vacuo
extractionthe residue is extracted 3 times with ethyl acetate
dry with materialAfter the ethyl acetate phase has been dried over sodium sulphate, it
customis evaporated in vacuo
customthe methyl 6-(3-carboxybicyclo[2.2.1]hept-2-yl)-hex-5-enoate is purified

Sources & evidence

ORD record: ord-4a964eaf196c4b1eaeb25ee00a7514e6
Source dataset: uspto-grants-1986_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04622339

Reaction notes

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