Diethyl Ether → HCID 13560729, compound

HRID 1285488Notes

Reaction equation

HRID 1285488 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:5]=[CH:6][CH:7]=1.[Cr](Cl)([O-])(=O)=O.[NH+:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:26]([O-])(=O)[CH3:27].[Na+].[CH3:31][CH2:32]OCC.[CH2:36](Cl)Cl>>[C:8]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[O:1][CH2:36][C:21]1[CH:22]=[CH:23][C:24]2[C:25](=[CH:31][CH:32]=[CH:26][CH:27]=2)[N:20]=1)(=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[C:8]([C:4]1[CH:3]=[C:2]([OH:1])[CH:7]=[CH:6][CH:5]=1)(=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 6344Dichloromethane2×HCID 517045Sodium AcetateHCID 117900843-(1-Hydroxyhexyl)phenolHCID 178418287HCID 178418287, compound

Product 2

HCID 13560729HCID 13560729, compoundHCID 143491261-(3-Hydroxyphenyl)hexan-1-one

Procedure

A solution of 1-(3-hydroxyphenyl)-1-hexanol (3 g) (made in Example 1B) in methylene chloride (200 ml) was added to a well-stirred suspension of pyridinium chlorochromate (5.1 g) and sodium acetate (2.5 g) in methylene-chloride (150 ml). The mixture was stirred at room temperature for two hours. Ether (100 ml) was added, and the brown granular precipitate was removed by filtration. All volatiles were removed from the filtrate, and the residual liquid was purified by chromatography on silical gel using ether as eluent. The desired ketone, 3-hexanoylphenol, was isolated as a clear, colorless oil.

Workup

  1. customthe brown granular precipitate was removed by filtration
  2. customAll volatiles were removed from the filtrate
  3. customthe residual liquid was purified by chromatography on silical gel

Sources & evidence

ORD record
ord-377e7a5afada46099193a9b330dbe64b
Source dataset
uspto-grants-1986_01
Patent number
US04567184

Reaction notes

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