3-Ethylphenol → (4-Ethyl-2-hydroxyphenyl)(4-fluorophenyl)methanone

HRID 1391331Notes

Reaction equation

HRID 1391331 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)[CH3:2].[F:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1>>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:15]([C:14]2[CH:18]=[CH:19][C:11]([F:10])=[CH:12][CH:13]=2)=[O:16])=[C:5]([OH:9])[CH:4]=1)[CH3:2]

Participants

3

Reactant 2

HCID 121013-EthylphenolHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 12562657(4-Ethyl-2-hydroxyphenyl)(4-fluorophenyl)methanoneYield 5.3%

Procedure

3-Ethylphenol (24.4 g) and 4-fluorobenzoyl chloride (34.9 g) were reacted together as in Example 2 giving three main fractions: B (11.4 g) 126°-129° C. at 0.07 mmHg; C (7.9 g), 129°-132° C. at 0.06 mmHg; D (5.9 g), 132°-150° C. at 0.06 mmHg, all containing ~ 80% of the required isomer. B (4.0 g) was separated by preparative thin layer chromatography to give the title compound (2.6 g), m.p. 44°-48° C. The same compound was obtained using the method of Example 4.

Workup

  1. customB (11.4 g) 126°-129° C.
  2. customC (7.9 g), 129°-132° C.
  3. customD (5.9 g), 132°-150° C.
  4. customB (4.0 g) was separated by preparative thin layer chromatography

Sources & evidence

ORD record
ord-aebf2600940247c2ba98b71cb7809372
Source dataset
uspto-grants-1979_02
Patent number
US04141995

Reaction notes

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