Methyl 3-methoxy-4-(2-methylallyloxy)benzoate → HCID 59560147, compound

HRID 1177371Notes

Reaction equation

HRID 1177371 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13]CC(C)=C)[C:6]([O:8][CH3:9])=[O:7]>CN1C(=O)CCC1>[OH:13][C:12]1[C:11]([CH2:6][C:5]([CH3:10])=[CH2:4])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

3

Reactant 1

HCID 51109732Methyl 3-methoxy-4-(2-methylallyloxy)benzoate

Product 1

HCID 59560147HCID 59560147, compoundYield 230.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of methyl 3-methoxy-4-(2-methylallyloxy)benzoate (130 g, 0.55 mol) in NMP (500 mL) was heated to reflux for 6 h. TLC (EtOAc/petroleum ether=1/5) showed the reaction was complete. The mixture was washed with 1 N aq. HCl and extracted with EtOAc (250 mL×3). The combined organic phases were washed with brine (400 mL), dried over Na2SO4 and concentrated to give the product (150 g, 100%) as a brown oil. The oil was used directly to the next step without further purification.

Workup

  1. temperatureto reflux for 6 h
  2. washThe mixture was washed with 1 N aq. HCl
  3. extractionextracted with EtOAc (250 mL×3)
  4. washThe combined organic phases were washed with brine (400 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6b2aa86244904ce1b90786eb206d0822
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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