Hydrochloric Acid → HCID 14852506, compound

HRID 1589974Notes

Reaction equation

HRID 1589974 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:26]=[CH:27][C:28]=3[OH:29])[C:14]([O:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Na+].[CH2:32](Br)[CH:33]=[CH2:34].Cl>O.CN(C=O)C.C1COCC1>[C:1]12([C:11]3[CH:12]=[C:13]([CH:26]=[CH:27][C:28]=3[O:29][CH2:34][CH:33]=[CH2:32])[C:14]([O:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)=[O:15])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 19372197HCID 19372197, compound

Product 1

HCID 14852506HCID 14852506, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.17 g (3 mmoles) of 4-[3-(1-adamantyl)-4-hydroxybenzoyloxy] benzoic acid in 100 ml of a 50:50 mixture of THF and DMF, there are added, by small portions, 180 mg (6 mmoles) of sodium hydride (80% in oil). The mixture is stirred at ambient temperature until the cessation of gaseous emission. There are then added 260 μl (3 mmoles) of allyl bromide and the mixture is stirred at ambient temperature for 3 hours. The reaction medium is poured into water, acidified to pH 4 with 1N HCl and extracted with ethyl ether. The organic phase, is decanted, washed with water, dried on magnesium sulfate and evaporated. The resulting residue is purified by chromatography on silica eluted with ethyl ether. After evaporation of the solvent, 880 mg (68% yield) of 4-[3-(1-adamantyl)-4-allyloxybenzoyloxy] benzoic acid having a melting point of 260°-261° C. are recovered.

Workup

  1. stirringthe mixture is stirred at ambient temperature for 3 hours
  2. extractionextracted with ethyl ether
  3. customThe organic phase, is decanted
  4. washwashed with water
  5. customdried on magnesium sulfate
  6. customevaporated
  7. customThe resulting residue is purified by chromatography on silica
  8. washeluted with ethyl ether

Sources & evidence

ORD record
ord-5ca323ea8eda4b90980487f7473508f5
Source dataset
uspto-grants-1993_04
Patent number
US05200550

Reaction notes

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