HCID 66981029, compound → HCID 66981058, compound

HRID 876201Notes

Reaction equation

HRID 876201 reaction equation
[CH:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([O:13]C)=[C:9]([O:15]C)[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>Br.C(O)(=O)C>[CH:1]1([CH2:6][C:7]2[CH:8]=[C:9]([OH:15])[C:10]([OH:13])=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 66981029HCID 66981029, compound

Product 1

HCID 66981058HCID 66981058, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution 4-(cyclopentylmethyl)-1,2-dimethoxybenzene (7.1 g, 0.032 mol) in 43 ml of hydrobromic acid (48% in water) and 4 ml of acetic acid was heated at 120° C. during 24 hours. The reaction mixture was cooled to room temperature and quenched with 50 ml of NH4Cl solution. The aqueous phase extracted with three 100 ml portions of ether. The ethereal phase was washed with 50 ml of brine and dried over MgSO4. Filtration and concentration gave 6.0 g (97%) of a brownish solid.

Workup

  1. customquenched with 50 ml of NH4Cl solution
  2. extractionThe aqueous phase extracted with three 100 ml portions of ether
  3. washThe ethereal phase was washed with 50 ml of brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-99a07d429ac44f819fb765efd5490fb6
Source dataset
uspto-grants-2015_03
Patent number
US08987188B2

Reaction notes

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