Sulfuric Acid → 2-(3,5-Dimethyladamantan-1-yl)acetic acid

HRID 2054561Notes

Reaction equation

HRID 2054561 reaction equation
S(=O)(=O)(O)[OH:2].B(F)(F)F.CC[O:12][CH2:13][CH3:14].Br[C:16]12[CH2:25][C:20]3([CH3:26])[CH2:21][CH:22]([CH2:24][C:18]([CH3:27])([CH2:19]3)[CH2:17]1)[CH2:23]2>ClC(Cl)=C>[CH3:27][C:18]12[CH2:24][CH:22]3[CH2:21][C:20]([CH3:26])([CH2:25][C:16]([CH2:14][C:13]([OH:12])=[O:2])([CH2:23]3)[CH2:17]1)[CH2:19]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8000Boron trifluoride etherateHCID 983171-Bromo-3,5-dimethyladamantane

Product 1

HCID 40675892-(3,5-Dimethyladamantan-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 6366Vinylidene chlorideSolvent

Conditions

Temperature
8 °C

Procedure

Concentrated sulfuric acid (44 mL) and boron trifluoride etherate (3.53 mL) were added to a flask and cooled to 8° C. A solution of 1-bromo-3,5-dimethyladamantane (11.02 g) in 1,1-dichloroethylene (35.3 mL) was added dropwise over a 2 hour period. The temperature was kept between 14 and 18° C. and gas evolution was observed. After stirring 1 hour at 10° C., the reaction was worked up by adding to ice and extracting with diethyl ether. The organic layer was extracted with 1N NaOH (3×), and the combined aqueous solution was acidified with sulfuric acid and re-extracted with ether (3×). The organic layers were combined, dried over magnesium sulfate, filtered and evaporated to dryness to give crude 3,5-dimethyladamantaneacetic acid (6.23 g).

Workup

  1. customwas kept between 14 and 18° C.
  2. additionby adding to ice
  3. extractionextracting with diethyl ether
  4. extractionThe organic layer was extracted with 1N NaOH (3×)
  5. extractionre-extracted with ether (3×)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-0a981473f0164866b0bb0c5289b3dd3f
Source dataset
uspto-grants-2008_02
Patent number
US07329683B2

Reaction notes

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