Hydrochloric Acid → HCID 14579737, compound

HRID 1607261Notes

Reaction equation

HRID 1607261 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([OH:15])=[C:8]([CH2:12][CH2:13][CH3:14])[CH:9]=[C:10]([Cl:11])[C:5]=2[O:4][C:3]=1C(O)=O.C1(C)C=CC=CC=1.Cl>C(O)(=O)C>[CH3:1][C:2]1[C:6]2[C:7]([OH:15])=[C:8]([CH2:12][CH2:13][CH3:14])[CH:9]=[C:10]([Cl:11])[C:5]=2[O:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 1140TolueneHCID 14579739HCID 14579739, compound

Product 1

HCID 14579737HCID 14579737, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-methyl-4-hydroxy-5-propyl--7-chlorobenzofuran carboxylic acid (0.93 gm; 3.7 mmoles), toluene (25 mL), 6N hydrochloric acid (20 mL), 10N HCl (100 mL) and acetic acid (30 ml) was refluxed for a period of 18 hours. The two phases were separated and the organic phase was dried (Na2SO4), and concentrated in vacuo to yield 3-methyl-4-hydroxy-5-propyl-7-chlorobenzofuran (0.62 gm; 80%), identical to the product obtained from the cyclisation reaction described above in Step C.

Workup

  1. temperaturewas refluxed for a period of 18 hours
  2. customThe two phases were separated
  3. dry with materialthe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25d070da4212492c9062ecf42fb8969c
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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