3-Chlorobenzoic Acid → HCID 117599307, compound

HRID 1466157Notes

Reaction equation

HRID 1466157 reaction equation
[OH:1][CH2:2]/[CH:3]=[CH:4]/[C:5]1[CH:14]=[CH:13][C:8]2[C:9](=[O:12])[O:10][CH2:11][C:7]=2[CH:6]=1.ClC1C=C(C=CC=1)C(O)=[O:20]>C(Cl)Cl>[OH:1][CH2:2][CH:3]1[O:20][CH:4]1[C:5]1[CH:14]=[CH:13][C:8]2[C:9](=[O:12])[O:10][CH2:11][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 4473-Chlorobenzoic AcidHCID 117599332HCID 117599332, compound

Product 1

HCID 117599307HCID 117599307, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-[(1E)-3-hydroxyprop-1-en-1-yl]-2-benzofuran-1(3H)-one (2.0 g, 10.5 mmol) in 50 mL of DCM was cooled to 0° C. and meta-chlorobenzoic acid (2.14 g, 10.53 mmol) in DCM (100 mL) was added dropwise. The temperature of the reaction mixture was then allowed to rise to RT. After 2 hours, the mixture was filtered and the filtrate was partitioned between DCM and water. The organic layer was washed with water (20 mL) and brine (20 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified with silica gel chromatography (petrol ether/EtOAc=2:1) to give the title product.

Workup

  1. customto rise to RT
  2. filtrationthe mixture was filtered
  3. customthe filtrate was partitioned between DCM and water
  4. washThe organic layer was washed with water (20 mL) and brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified with silica gel chromatography (petrol ether/EtOAc=2:1)

Sources & evidence

ORD record
ord-c26f296469ed4ee39dd78ea2d7348e09
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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