HCID 4130341, compound → 2-(3-thienyl)phenol

HRID 1272207Notes

Reaction equation

HRID 1272207 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:12]C)=[CH:2]1.Cl.[NH+]1C=CC=CC=1>>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[OH:12])=[CH:2]1

Participants

3

Reactant 2

HCID 4130341HCID 4130341, compoundHCID 21584435Pyridinium hydrochloride

Product 1

HCID 41303442-(3-thienyl)phenolYield 99.3%

Procedure

An intimate mixture of 2-(thien-3-yl)anisole (1.2 g, 4 mmol) and 6.0 g (50 mmol) of pyridinium hydrochloride is heated for 20 minutes to 200° C. (1000 W MW, microwave). The mixture is allowed to cool to room temperature then is extracted with ethyl acetate and dichloromethane. The organic extracts are washed with water, dried over sodium sulfate and evaporated. The residue is purified via flash column on silica (eluent: 100% hexane>hexane/ethyl acetate 9:1 gradient) to give 700 mg of 2-(thien-3-yl)phenol (97%). M+=176.

Workup

  1. temperatureis heated for 20 minutes to 200° C. (1000 W MW, microwave)
  2. extractionthen is extracted with ethyl acetate and dichloromethane
  3. washThe organic extracts are washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue is purified via flash column on silica (eluent: 100% hexane>hexane/ethyl acetate 9:1 gradient)

Sources & evidence

ORD record
ord-c0207600923a4890ae5fef0a3f998e60
Source dataset
uspto-grants-2007_04
Patent number
US07208505B2

Reaction notes

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