Diethyl Ether → 3-Phenoxyphenyl ethyl ketone

HRID 1907018Notes

Reaction equation

HRID 1907018 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]([OH:17])[CH2:15][CH3:16])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)C.[Cr](O)(O)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[O:1]([C:8]1[CH:9]=[C:10]([C:14](=[O:17])[CH2:15][CH3:16])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 10340Sodium CarbonateHCID 24425Chromic AcidHCID 151854771-(3-Phenoxyphenyl)propan-1-ol

Product 1

HCID 108679943-Phenoxyphenyl ethyl ketone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 35 g of 1-(3-phenoxyphenyl)propan-1-ol and 50 ml of ethyl ether is treated with 1.1 equivalants of chromic acid, which is added dropwise over a 30 minute period. The reaction mixture is allowed to warm to 20°-25° C. and stirred for about 2 hours. Then the reaction mixture is added to a mixture of 25 ml of ethyl ether and 50 ml of water, and sodium carbonate is slowly added to neutralize the acid. The phases are separated and the aqueous phase is reextracted twice with ethyl ether. The ethereal extracts are combined and evaporated under reduced pressure to yield 1-(3-phenoxyphenyl)-propan-1-one as an oil.

Workup

  1. additionis added dropwise over a 30 minute period
  2. temperatureto warm to 20°-25° C.
  3. additionis slowly added
  4. customThe phases are separated
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-599bb8e57ab140b9a2ddb266807e6824
Source dataset
uspto-grants-1987_03
Patent number
US04654438

Reaction notes

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