Hydrochloric Acid → HCID 15021928, compound

HRID 1154864Notes

Reaction equation

HRID 1154864 reaction equation
Br[CH:2]([CH3:4])[CH3:3].[CH3:5][C:6]1([CH3:17])[CH2:10][C:9]2[CH:11]=[CH:12][C:13]([CH:15]=[O:16])=[CH:14][C:8]=2[O:7]1.[Cl-].[NH4+].Cl>O1CCCC1>[CH3:5][C:6]1([CH3:17])[CH2:10][C:9]2[CH:11]=[CH:12][C:13]([CH:15]([CH:2]([CH3:4])[CH3:3])[OH:16])=[CH:14][C:8]=2[O:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 63582-BromopropaneHCID 25517Ammonium ChlorideHCID 12879983HCID 12879983, compound

Product 1

HCID 15021928HCID 15021928, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

18.7 g of 2-bromopropane in 30 ml of absolute tetrahydrofuran are added dropwise to 3.6 g of Mg filings in 15 ml of absolute tetrahydrofuran. The mixture is stirred under reflux for 1 hour and is then cooled to 5°-10° C. At this temperature, 23 g of 2,2-dimethyl-2,3-dihydrobenzofuran-6-aldehyde in 100 ml of absolute tetrahydrofuran are added dropwise. The reaction mixture is stirred overnight and is then cautiously decomposed with a cold saturated ammonium chloride solution and a few milliliters of 10% strength hydrochloric acid, sufficient to dissolve the precipitate. The mixture is then extracted three times by shaking with ether and the combined ether extracts are washed with sodium bisulfate solution, sodium bicarbonate solution and water, dried over sodium sulfate and concentrated under reduced pressure. 19.5 g of 2,2-dimethyl-2,3-dihydrobenzofuran-6-yl-(α-isopropyl)-carbinol are obtained in the form of a yellowish oil, which is sufficiently pure for the subsequent reactions. (Yield 68%).

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureis then cooled to 5°-10° C
  3. stirringThe reaction mixture is stirred overnight
  4. dissolutionsufficient to dissolve the precipitate
  5. extractionThe mixture is then extracted three times
  6. stirringby shaking with ether
  7. washthe combined ether extracts are washed with sodium bisulfate solution, sodium bicarbonate solution and water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e96519ee81a641c290bfb250f0a56d8e
Source dataset
uspto-grants-1981_11
Patent number
US04298615

Reaction notes

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