1-Tetralone → ST50113612

HRID 576490Notes

Reaction equation

HRID 576490 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[OH-].[K+]>O1CCCC1.CO>[Br:12][C:13]1[CH:20]=[CH:19][C:16](/[CH:17]=[C:2]2/[C:1](=[O:11])[C:10]3[C:5]([CH2:4][CH2:3]/2)=[CH:6][CH:7]=[CH:8][CH:9]=3)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 107241-TetraloneHCID 14797Potassium HydroxideHCID 707414-Bromobenzaldehyde

Product 1

HCID 1549209ST50113612Yield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 250 mL flask was charged with tetralone (3.22 g, 22 mmol) and 4-bromobenzaldehyde (5.3 g, 28.6 mmol). This was dissolved in warm tetrahydrofuran (12 mL), and to this yellow solution was slowly added a 4 wt % solution of KOH in methanol (100 mL). The reaction was stirred for 4 days at room temperature. The mixture was concentrated and reduced to approx 10% vol. The residue was filtered and washed with MTBE (3*50 mL), dried, to afford a light yellow powder (6.61 g, 96%).

Workup

  1. concentrationThe mixture was concentrated
  2. filtrationThe residue was filtered
  3. washwashed with MTBE (3*50 mL)
  4. customdried

Sources & evidence

ORD record
ord-d7cc6d1dbe2549e3ba7b865c93fc5fdd
Source dataset
uspto-grants-2015_05
Patent number
US09040175B2

Reaction notes

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