Phosphoric Acid → 1-(4-Fluorophenyl)-1,3-dihydroisobenzofuran

HRID 846767Notes

Reaction equation

HRID 846767 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[C:11]([CH2:16][OH:17])=[CH:12][CH:13]=[CH:14][CH:15]=2)O)=[CH:4][CH:3]=1.P(=O)(O)(O)O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:10]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:16][O:17]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 1004Phosphoric AcidHCID 14230258alpha-(4-Fluorophenyl)-1,2-benzenedimethanol

Product 1

HCID 142302591-(4-Fluorophenyl)-1,3-dihydroisobenzofuran

Conditions

Temperature
100 °C

Procedure

A mixture of 200 parts of α-(4-fluorophenyl)-1,2-benzenedimethanol and 2295 parts of phosphoric acid 60% was stirred for 3 hours at 100° C. Stirring was continued overnight at room temperature. The reaction mixture was poured onto water and the product was extracted twice with 1,1'-oxybisethane. The combined extracts were washed with water, with a 10% sodium carbonate solution and again with water, dried, filtered and evaporated. The residue was distilled, yielding 57 parts of 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran; bp. 108° C. at 0.2 mm. pressure (intermediate 92).

Workup

  1. stirringStirring
  2. waitwas continued overnight at room temperature
  3. additionThe reaction mixture was poured onto water
  4. extractionthe product was extracted twice with 1,1'-oxybisethane
  5. washThe combined extracts were washed with water, with a 10% sodium carbonate solution and again with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. distillationThe residue was distilled

Sources & evidence

ORD record
ord-e223cc77aab9446a9d1b29408a71fd33
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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