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

HRID 1606018Notes

Reaction equation

HRID 1606018 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 (24.4g) and 4-fluorobenzoyl chloride (34.9g) were reacted together as in Example 11 giving three main fractions: B (11.4g) 126°-129°C at 0.07 mmHg; C (7.9g), 129°-132°C at 0.06 mmHg; D (5.9g), 132°-150°C at 0.06 mmHg, all containing ~80% of the required isomer. B (4.0g) was separated by preparative thin layer chromatography to give the title compound (2.6g), m.p. 44°-48°C.

Workup

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

Sources & evidence

ORD record
ord-37bfe15f09714ba685a5c03749ea8082
Source dataset
uspto-grants-1976_04
Patent number
US03951999

Reaction notes

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