Methanesulfonic Acid → 2-Methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one

HRID 1163289Notes

Reaction equation

HRID 1163289 reaction equation
[P+3]=O.CS(O)(=O)=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=O)[CH:13]=[CH:14][CH:15]=1>O>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]2[C:20](=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 105844855-(3-methoxyphenyl)pentanoic AcidHCID 178526999HCID 178526999, compound

Product 1

HCID 2668152-Methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-oneYield 83.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of phosphorus(V) oxide (10 g) and methanesulfonic acid (70 mL) was stirred at 100° C. for 1 hr. The obtained solution and 5-(3-methoxyphenyl)pentanoic acid (5.28 g, 25.4 mmol) were mixed and the mixture was stirred for 1 hr. The reaction mixture was poured into iced water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-30% ethyl acetate/hexane) to give the title compound (4.02 g, 83%) as a red-brown oil.

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e331377740b64437a0acd8246bc85d7b
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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