Catechol → HCID 68972901, compound

HRID 1726267Notes

Reaction equation

HRID 1726267 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:24]1([C:26](=[CH:28][CH:29]=[CH:30][CH:31]=1)O)[OH:25].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C(C)=CC=CC=1>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]2([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[O:23][C:31]3[CH:30]=[CH:29][CH:28]=[CH:26][C:24]=3[O:25]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 289CatecholHCID 521998p-Toluenesulfonic acid monohydrateHCID 49760136tert-Butyl 4-(4-methoxybenzoyl)piperidine-1-carboxylate

Product 1

HCID 68972901HCID 68972901, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of the above ketone (957 mg, 3.00 mmol), catechol (660 mg, 6.00 mmol) and p-TsOH.H2O (1.14 g, 6.00 mmol) in xylene (20 mL) was heated at reflux using a Dean-Stark apparatus to remove water for 24 hours. Standard work-up and purification gave 4-[2-(4-methoxy-phenyl)-benzo[1,3]dioxol-2-yl]-piperidine as a pale yellow oil (335 mg, 36%).

Workup

  1. temperatureat reflux
  2. customto remove water for 24 hours
  3. customStandard work-up and purification

Sources & evidence

ORD record
ord-d94b9e0bf74742269cc86473f0e2fd20
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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