p-Toluenesulfonic acid → HCID 66998483, compound

HRID 560321Notes

Reaction equation

HRID 560321 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([Cl:16])=[C:10]2[O:14][CH:13](O)[CH2:12][C:11]=12)=[O:5])[CH3:2].C(OC(C1C=CC(Cl)=C2OC(OC)CC=12)=O)C.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([Cl:16])=[C:10]2[O:14][CH:13]=[CH:12][C:11]=12)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acid2×HCID 66998395HCID 66998395, compoundHCID 66998604HCID 66998604, compound

Product 1

HCID 66998483HCID 66998483, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 7-chloro-2-hydroxy-2,3-dihydro-benzofuran-4-carboxylic acid ethyl ester and 7-chloro-2-methoxy-2,3-dihydro-benzofuran-4-carboxylic acid ethyl ester (3.36 g, see above) in toluene (20 mL) is added dropwise to a solution of PTSA (0.69 mmol) in toluene (14 mL) which is heated to reflux. Heating is continued for 5 h, an additional portion of PTSA (0.69 mmol) is added and the mixture is again heated to reflux for 150 min. The solvents are removed in vacuo and the residue is purified by FC (gradient: heptane to heptane/EtOAc 95/5) to give the desired product.

Workup

  1. temperatureis heated to reflux
  2. temperatureHeating
  3. temperaturethe mixture is again heated
  4. temperatureto reflux for 150 min
  5. customThe solvents are removed in vacuo
  6. customthe residue is purified by FC (gradient: heptane to heptane/EtOAc 95/5)

Sources & evidence

ORD record
ord-b46916ea52124be1a1c0422def33cbd0
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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