Hydrochloric Acid → HCID 53661838, compound

HRID 1733487Notes

Reaction equation

HRID 1733487 reaction equation
Br[CH2:2][CH3:3].[Mg].C#C.[F:7][C:8]1[CH:22]=[CH:21][C:11]([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[CH:16]=[O:17])=[CH:10][CH:9]=1.C([Mg]Br)#C.Cl>O1CCCC1>[F:7][C:8]1[CH:22]=[CH:21][C:11]([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[CH:16]([OH:17])[C:2]#[CH:3])=[CH:10][CH:9]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6326Acetylene2×HCID 6332Ethyl BromideHCID 3085320Benzaldehyde, 3-(4-fluorophenoxy)-HCID 5462224MagnesiumHCID 178418486HCID 178418486, compound

Product 1

HCID 53661838HCID 53661838, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
50 °C

Procedure

14 g (0.13 mol) of bromoethane were slowly added dropwise, while stirring, to 2.4 g (0.1 mol) of magnesium filings in 70 ml of anhydrous tetrahydrofuran at 30°-40° C. and the mixture was then stirred for a further 30 minutes at 50° C. The Grignard solution thus prepared was transferred into a dropping funnel under nitrogen and was added dropwise to a saturated solution of acetylene in 40 ml of anhydrous tetrahydrofuran, the solution having been saturated at 20° C. During the addition further acetylene was passed in continuously, and this was continued for a further 30-45 minutes after the end of the dropwise addition. 10.8 g (0.05 mol) of 3-(4-fluorophenoxy)-benzaldehyde, dissolved in 50 ml of absolute tetrahydrofuran, were added dropwise to the suspension of ethynyl magnesium bromide, thus prepared, at 25°-30° C., and the mixture was then warmed to 40° C. for 4 hours. Thereafter the reaction batch was cooled to 10° C. and poured into 500 ml of ice-water, and the resulting precipitate was dissolved by adding concentrated hydrochloric acid. The mixture was then extracted twice with 150 ml of ether at a time, the ether phases were dried over sodium sulfate and the ether was then distilled off in vacuo. 7.3 g (61% of theory) of 3-(4-fluorophenoxy)-α-ethynyl-benzyl alcohol were obtained as a yellow oil of boiling point 160°-180° C./3 mm Hg. ##STR27##

Workup

  1. customThe Grignard solution thus prepared
  2. customwas transferred into a dropping funnel under nitrogen
  3. customhaving been saturated at 20° C
  4. waitthis was continued for a further 30-45 minutes
  5. additionafter the end of the dropwise addition
  6. customthus prepared, at 25°-30° C.
  7. temperaturethe mixture was then warmed to 40° C. for 4 hours
  8. temperatureThereafter the reaction batch was cooled to 10° C.
  9. dissolutionthe resulting precipitate was dissolved
  10. extractionThe mixture was then extracted twice with 150 ml of ether at a time
  11. dry with materialthe ether phases were dried over sodium sulfate
  12. distillationthe ether was then distilled off in vacuo

Sources & evidence

ORD record
ord-1cc175816d0f4a14a757ff44d8450323
Source dataset
uspto-grants-1980_12
Patent number
US04242357

Reaction notes

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