1-Tetralone → 7-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

HRID 328605Notes

Reaction equation

HRID 328605 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:4][CH:3]=1.C1(=O)C2C(=CC=CC=2)CCC1>>[F:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][CH2:9][CH2:10][C:11]2=[O:13])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 107241-TetraloneHCID 685244-(p-Fluorophenyl)butyric acid

Product 1

HCID 103747647-Fluoro-1,2,3,4-tetrahydronaphthalen-1-oneYield 63.2%

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 4-(p-fluorophenyl) butanoic acid (23g; 0.126 mole) and 85% polyphosphoric acid (200g) was heated at 100° C for 4 hrs., cooled, and poured onto ice-water (800g). After through stirring the precipitated tetralone was filtered off, washed well with water, and recrystallised from ethanol to give 13.07g (63%) of material of m.p. 56°-57° C. (Found; C, 73.31; H, 5.72; C10H9FO requires; C, 73.13; H, 5,53%).

Workup

  1. temperature, cooled
  2. filtrationwas filtered off
  3. washwashed well with water
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-8db7eff4cb764ffb9ffcf1f07abb8181
Source dataset
uspto-grants-1977_04
Patent number
US04017639

Reaction notes

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