Ethane → 3-Phenoxy-alpha-ethynylbenzylalcohol

HRID 2050099Notes

Reaction equation

HRID 2050099 reaction equation
[CH2:1]([Mg]Br)[CH3:2].CC.C#C.[O:9]([C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[O:20])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+]>C1COCC1>[C:1]([CH:19]([OH:20])[C:18]1[CH:21]=[CH:22][CH:23]=[C:16]([O:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:17]=1)#[CH:2]

Participants

7

Reactant 5

HCID 6324EthaneHCID 6326AcetyleneHCID 25517Ammonium ChlorideHCID 382843-PhenoxybenzaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 129190923-Phenoxy-alpha-ethynylbenzylalcoholYield 68.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetylene is dried through three traps, dry-ice-acetone, concentrated sulfuric acid and calcium chloride, and bubbled at about 5 psi pressure into dry THF (100 ml) for 10 minutes. Ethyl magnesium bromide (commercial, 0.14 mol) is added drop after drop over 2 hours at such a rate that the evolution of ethane is slowly and steady. After the addition, acetylene is bubbled through for 15 minutes. m-Phenoxybenzaldehyde (27.7 g, 0.14 mol) in THF (25 ml) is added to the reaction of 15° to 20° C. The reaction is allowed to raise to room temperature and stirred overnight. The complex is decomposed with saturated ammonium chloride solution. The product is extracted with ether, washed with water and dried (Na2SO4). Evaporation of the solvents, followed by vacuum distillation using Kugelrohn gives the alcohol (21.5 g).

Workup

  1. dry with materialAcetylene is dried through three traps, dry-ice-acetone, concentrated sulfuric acid and calcium chloride
  2. custombubbled at about 5 psi pressure into dry THF (100 ml) for 10 minutes
  3. customis bubbled through for 15 minutes
  4. extractionThe product is extracted with ether
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvents
  8. distillationfollowed by vacuum distillation

Sources & evidence

ORD record
ord-371a61666ecc4f2c84a0377193886c11
Source dataset
uspto-grants-1980_04
Patent number
US04199595

Reaction notes

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