Water → HCID 20222014, compound

HRID 980081Notes

Reaction equation

HRID 980081 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[Cl:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[CH:30]([CH2:32][CH2:33][CH:34]([OH:36])[CH3:35])[CH3:31].O>CN(C)C=O>[Cl:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[C:30]([CH2:32][CH2:33][C:34](=[O:36])[CH3:35])=[CH2:31]

Participants

5

Reactant 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 20222006HCID 20222006, compound

Product 1

HCID 20222014HCID 20222014, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of pyridinium dichromate (49 g) and 2-(2,4-dichlorophenyl)hexan-5-ol (16 g) in dry dimethylformamide (100 ml) was stirred overnight at room temperature then poured into water and extracted with ether. The extracts were washed successively with dilute hydrochloric acid and water, then dried over magnesium sulphate and concentrated under reduced pressure to give almost pure 2-(2,4-dichlorophenyl)hex-1-en-5-one (14.5 g, 91%) as a yellow oil, 1H n.m.r. (CDCl3): δ2.18 (3H,s), 2.4-3.0 (4H,m), 5.15 (1H,s), 5.41 (1H,s), 7.2-7.6 (3H, m).

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed successively with dilute hydrochloric acid and water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-584d2b734ac544009d5b8b32da016993
Source dataset
uspto-grants-1987_01
Patent number
US04636247

Reaction notes

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