Hydrochloric Acid → 4-Hydroxybicyclo[2.2.2]octane-1-carboxylic acid

HRID 2280741Notes

Reaction equation

HRID 2280741 reaction equation
Br[C:2]12[CH2:9][CH2:8][C:5]([C:10]([O:12]C)=[O:11])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.Cl.[OH-:15].[Na+]>>[OH:15][C:2]12[CH2:9][CH2:8][C:5]([C:10]([OH:12])=[O:11])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57467434Methyl 4-bromobicyclo(2.2.2)octane-1-carboxylate

Product 1

HCID 125601364-Hydroxybicyclo[2.2.2]octane-1-carboxylic acidYield 89%

Procedure

Methyl 4-bromobicyclo[2.2.2]octane-1-carboxylate (17.0 g, 69.0 mol) was refluxed in aqueous sodium hydroxide solution (1500 mL, 1%) for 24 h. After cooling, the reaction solution was acidified with hydrochloric acid (6 N, 100 mL) and extracted with diethyl ether (6×500 mL). The combined ether layers were dried over magnesium sulfate and concentrated to afford the title compound (10.4 g, 61.1 mmol, 89% yield), which was used in the next step without further purification. MS (ESI) m/z 169.2 [M+H]−.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether (6×500 mL)
  3. dry with materialThe combined ether layers were dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c64da989ae784c5bae369ced1f8e43e8
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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