Hydrochloric Acid → 19082-37-2

HRID 2352503Notes

Reaction equation

HRID 2352503 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9]([OH:14])[CH2:10][CH2:11][C:12]#[CH:13].[Cl-].[NH4+].Cl>C(OCC)C>[OH:14][CH:9]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:10][CH2:11][C:12]#[CH:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 793464-Pentyn-1-olHCID 178418255HCID 178418255, compound

Product 1

HCID 1257135519082-37-2Yield 58%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an ice-cold solution of 3.0M phenylmagnesium bromide (100 mL, 300 mmol) under argon atmosphere was added dropwise pent-4-yn-1-ol (10 g, 120 mmol) in diethyl ether (20 mL). After stirring for 3 hours the solution was slowly added to an ice-cold solution of dilute ammonium chloride. 6N Hydrochloric acid was added to break up the gel and the layers were separated. The aqueous extract was washed with diethyl ether (3×50 mL) and the combined organic extracts were washed with brine and dried (MgSO4). The solvent was removed by rotary evaporation under reduced pressure to give 17 g of the crude product which was Kugelrohr distilled to afford 11.1 g (58%) of the purified product. 1H NMR (CDCl3) δ: 1.82-1.95 (m, 2H), 1.98 (t, 1H), 2.20-2.35 (m, 2H), 2.40 (s, 1H), 4.80-4.85 (m, 1H), 7.30-7.38 (m, 5H) ppm.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous extract
  3. washwas washed with diethyl ether (3×50 mL)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed by rotary evaporation under reduced pressure
  7. customto give 17 g of the crude product which
  8. distillationdistilled

Sources & evidence

ORD record
ord-4615f9a7b4aa441e81d5fdcc477f8554
Source dataset
uspto-grants-1989_10
Patent number
US04877779

Reaction notes

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