Tetrahydrofuran → 4-(4-Bromophenyl)cyclohexane-1-carbaldehyde

HRID 1975615Notes

Reaction equation

HRID 1975615 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][C:11](=[CH:14][O:15]C)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O1CCCC1>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][CH:11]([CH:14]=[O:15])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 190979141-Bromo-4-[4-(methoxymethylidene)cyclohexyl]benzene

Product 1

HCID 190979014-(4-Bromophenyl)cyclohexane-1-carbaldehydeYield 95.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10.4 g of 1-bromo-4-[4-(methoxymethyli-dene)cyclohexyl]benzene and 100 ml of tetrahydrofuran/2N hydrochloric acid (vol. 4:1) was heated to reflux for 30 minutes in a round flask. Subsequently, the reaction mixture was poured into 100 ml of water and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed with 100 ml of water, dried over magnesium sulphate and concentrated. There were obtained 9.4 g of 4-(4-bromophenyl)cyclohexanecarboxaldehyde as white crystals; trans/cis ratio about 5:3.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes in a round flask
  3. extractionextracted three times with 100 ml of diethyl ether each time
  4. washThe organic phases were washed with 100 ml of water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1ccd38fd5d124569bac9e683f3bf82a6
Source dataset
uspto-grants-1994_02
Patent number
US05288428

Reaction notes

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