Hydrochloric Acid → Methyl 2-hydroxy-2-phenylpent-3-ynoate

HRID 358243

Reaction equation

HRID 358243 reaction equation
[C:1]([Mg]Br)#[C:2][CH3:3].[Mg].C(Br)C.C#CC.[C:13]1([C:19](=[O:24])[C:20]([O:22][CH3:23])=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>CCOCC.C1COCC1>[C:13]1([C:19]([C:1]#[C:2][CH3:3])([OH:24])[C:20]([O:22][CH3:23])=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 6335PropyneHCID 84835Methyl phenylglyoxalateHCID 5462224MagnesiumHCID 178419101HCID 178419101, compound

Product 1

HCID 271980Methyl 2-hydroxy-2-phenylpent-3-ynoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1-Propynylmagnesium bromide (0.2 mole) was made from magnesium (4.8 g., 0.2 g. atom) ethyl bromide (21.8 g., 0.2 mole) and excess propyne gas in 400 ml. of THF. The Grignard reagent then was siphoned under nitrogen into an addition funnel and added dropwise over a 40 minute period to a cooled solution of methyl phenylglyoxylate (32.8 g., 0.2 mole) in 200 ml. of THF. A slight temperature rise took place. The reaction mixture was stirred for 24 hours, and then poured onto a slurry of ice and 25 ml. conc. HCl. Ether was added, and the layers were separated. Several more ether extracts were made and the organic extracts combined and dried. The volatile components were stripped subsequently in vacuo and the residue distilled to yield 13.1 g. (32%) of the product, b.p. 109°-12° (0.2 mm.). The oil solidified on standing and melted at 64°-65° after recrystallization from 20°-40° petroleum ether.

Workup

  1. additionpoured onto a slurry of ice and 25 ml
  2. customthe layers were separated
  3. customdried
  4. distillationthe residue distilled
  5. customto yield 13.1 g
  6. custommelted at 64°-65° after recrystallization from 20°-40° petroleum ether

Sources & evidence

ORD record
ord-cddf046e23764c22ab1722be07cde170
Source dataset
uspto-grants-1984_08
Patent number
US04465834

Linked notes

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