p-Toluenesulfonic acid → HCID 72547172, compound

HRID 1506855Notes

Reaction equation

HRID 1506855 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]([OH:13])=[O:12])[O:8][C:7]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:6]=2[CH:26]=1.[C:27]1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CO>[CH3:27][O:12][C:11]([CH:9]1[O:8][C:7]([CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:6]2[CH:26]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:10]1)=[O:13]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 13076901HCID 13076901, compound

Product 1

HCID 72547172HCID 72547172, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2 g 6-chloro-4,4-dicyclohexyl-4H-benzo[1,3]dioxine-2-carboxylic acid and 73 mg para-toluenesulfonic acid in 4 ml methanol was refluxed for 4 hours. After cooling to room temperature, 50 mg sodium bicarbonate was added and the solvent was removed in vacuo. The residue was dissolved in 10 ml EtOAc, washed with water and dried over Na2SO4. The solvent was removed in vacuo. Yield 1.3 g.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in 10 ml EtOAc
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-797e830e84644bc7848b354f029fb2ca
Source dataset
uspto-grants-2015_12
Patent number
US09221784B2

Reaction notes

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