3-Benzoylbenzaldehyde → HCID 13102753, compound

HRID 2164435Notes

Reaction equation

HRID 2164435 reaction equation
[C:1]([Mg]Br)#[CH:2].[C:5]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O1CCCC1>[C:1]([CH:16]([OH:17])[C:15]1[CH:18]=[CH:19][CH:20]=[C:13]([C:5](=[O:12])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:14]=1)#[CH:2]

Participants

4

Reactant 2

HCID 130201683-BenzoylbenzaldehydeHCID 178418486HCID 178418486, compound

Product 1

HCID 13102753HCID 13102753, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethynylmagnesium bromide (11.2 mmol) in tetrahydrofuran (20 cm3) was added dropwise to a stirred solution of 3-benzoylbenzaldehyde (2 g, 9.5 mmol, prepared as in Example 3(b) in tetrahydrofuran (30 cm3) through which purified acetylene was being passed. After 2 hours, saturated ammonium chloride solution (200 cm3) was added, and the mixture extracted with ether (3×50 cm3). The combined extracts were washed with saturated sodium chloride, dried over anhydrous sodium sulphate, and the solvent removed in vacuo. The product was purified by thin layer chromatography on silica to give the title alcohol, yield 1.1 g (49%) nD20 1.6075.

Workup

  1. custompurified acetylene
  2. additionsaturated ammonium chloride solution (200 cm3) was added
  3. extractionthe mixture extracted with ether (3×50 cm3)
  4. washThe combined extracts were washed with saturated sodium chloride
  5. dry with materialdried over anhydrous sodium sulphate
  6. customthe solvent removed in vacuo
  7. customThe product was purified by thin layer chromatography on silica

Sources & evidence

ORD record
ord-b6af8858aa2d42aeb42065e78db42027
Source dataset
uspto-grants-1985_03
Patent number
US04504491

Reaction notes

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