Sodium Hydroxide → (2E)-(6-Chlorospiro[chromene-2,1'-cyclobutan]-4(3H)-ylidene)acetic acid

HRID 453926Notes

Reaction equation

HRID 453926 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH2:6]/[C:5]/2=[CH:15]\[C:16]([O:18]CC)=[O:17].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[O:11][C:7]1([CH2:8][CH2:9][CH2:10]1)[CH2:6]/[C:5]/2=[CH:15]\[C:16]([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86652760Ethyl (2E)-(6-chlorospiro[chromene-2,1'-cyclobutan]-4(3H)-ylidene)acetate

Product 1

HCID 67107502(2E)-(6-Chlorospiro[chromene-2,1'-cyclobutan]-4(3H)-ylidene)acetic acidYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl (2E)-(6-chlorospiro[chromene-2,1′-cyclobutan]-4(3H)-ylidene)acetate (3 g, 10.22 mmol) in ethanol (30 ml) was added 1N sodium hydroxide solution (30 ml) at room temperature. The reaction mixture was stirred at room temperature for 2 h. The residue obtained after the evaporation of the solvent under reduced pressure was acidified with 1N HCl. The desired product was extracted into ethyl acetate (3×50 ml), washed with water (100 ml), brine, dried (Na2SO4) and concentrated to give 2.6 g of the product as a white solid; 1H NMR (300 MHz, CDCl3) δ 1.68-1.78 (m, 5H), 1.86-1.96 (m, 1H), 3.96 (s, 2H), 6.36 (s, 1H), 6.80 (d, J=8.1 Hz, 1H), 7.22 (d, J=9.3 Hz, 1H), 7.51 (s, 1H).

Workup

  1. customThe residue obtained
  2. customafter the evaporation of the solvent under reduced pressure
  3. extractionThe desired product was extracted into ethyl acetate (3×50 ml)
  4. washwashed with water (100 ml), brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6900c317144c4b35921c9a7860c7bf0e
Source dataset
uspto-grants-2013_07
Patent number
US08492568B2

Reaction notes

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