1-Tetralone → 244613-09-0

HRID 576491Notes

Reaction equation

HRID 576491 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:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.[OH-].[K+]>O1CCCC1.CO>[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)/[CH:16]=[C:2]1/[C:1](=[O:11])[C:10]2[C:5]([CH2:4][CH2:3]/1)=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

6

Reactant 3

HCID 107241-TetraloneHCID 14797Potassium HydroxideHCID 765833-Bromobenzaldehyde

Product 1

HCID 1811469244613-09-0Yield 92.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 250 mL flask was charged with tetralone (5.2 g, 35.6 mmol) and 3-bromobenzaldehyde (8.51 g, 56 mmol). This was dissolved in warm tetrahydrofuran (20 mL), and to this yellow solution was slowly added a 4 wt % solution of KOH in methanol (160 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 (10.3 g, 92%).

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-dc070051e6f244b4bb05f1b2a459ab9b
Source dataset
uspto-grants-2015_05
Patent number
US09040175B2

Reaction notes

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