Methyl 4-hydroxy-3-methoxy-5-(2-methylallyl)benzoate → Methyl 7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-carboxylate

HRID 1177372Notes

Reaction equation

HRID 1177372 reaction equation
[OH:1][C:2]1[C:11]([CH2:12][C:13]([CH3:15])=[CH2:14])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:16][CH3:17]>Cl.CO>[CH3:17][O:16][C:3]1[C:2]2[O:1][C:13]([CH3:15])([CH3:14])[CH2:12][C:11]=2[CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=1

Participants

4

Reactant 1

HCID 59560147Methyl 4-hydroxy-3-methoxy-5-(2-methylallyl)benzoate

Product 1

HCID 59560140Methyl 7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-carboxylateYield 53.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of methyl 4-hydroxy-3-methoxy-5-(2-methylallyl)benzoate (150 g, 0.63 mol) in conc. HCl (300 mL) and MeOH (300 mL) was heated to reflux for 2 h. TLC (EtOAc/petroleum ether=1/5) showed the reaction was complete. The solution was evaporated, and the residue was extracted with EtOAc (200 mL×3). The combined organic phases were washed with brine (200 mL), dried over Na2SO4 and concentrated to give a brown oil. The crude oil was purified by column chromatography (EtOAc/petroleum ether=1/30) to give the title compound (80 g, 53%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.51 (s, 1H), 7.46 (s, 1H), 3.91 (s, 3H), 3.87 (s, 3H), 3.05 (s, 2H), 1.53 (s, 6H).

Workup

  1. temperatureto reflux for 2 h
  2. customThe solution was evaporated
  3. extractionthe residue was extracted with EtOAc (200 mL×3)
  4. washThe combined organic phases were washed with brine (200 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give a brown oil
  8. customThe crude oil was purified by column chromatography (EtOAc/petroleum ether=1/30)

Sources & evidence

ORD record
ord-215b07f25d864e8bac70454e1b609969
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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