Hydrochloric Acid → Methyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylate

HRID 1177068Notes

Reaction equation

HRID 1177068 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([O:10]COC)[C:7]([CH2:14][C:15]([CH3:17])=[CH2:16])=[C:6]([O:18]COC)[CH:5]=1.Cl>CO>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([OH:10])[C:7]2[CH2:14][C:15]([CH3:17])([CH3:16])[O:18][C:6]=2[CH:5]=1)=[O:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59560052Methyl 3,5-bis(methoxymethoxy)-4-(2-methylallyl)benzoate

Product 1

HCID 25067323Methyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylateYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,5-bis-methoxymethoxy-4-(2-methyl-allyl)-benzoic acid methyl ester (31) (3.6 g, 9.02 mmol) in methanol (5 mL) was added 1.3 mL concentrated aqueous HCl. The reaction mixture was heated to reflux for 1 hr, quenched with H2O (100 mL), extracted with EtOAc (2×100 mL), dried over MgSO4 and concentrated. The residue was purified by flash column chromatography eluting with 5% EtOAc in hexane to give a pale yellow solid (1.08 g, 54% yield). 1H NMR (400 MHz, CDCl3) δ 7.12 (d, J=1.26 Hz, 1 H) 7.00 (d, J=1.01 Hz, 1 H) 5.63 (s, 1 H) 3.89 (s, 3 H) 3.00 (s, 2 H) 1.50 (s, 6 H); LCMS for C12H14O4 m/z 223.10 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hr
  3. customquenched with H2O (100 mL)
  4. extractionextracted with EtOAc (2×100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography
  8. washeluting with 5% EtOAc in hexane

Sources & evidence

ORD record
ord-8a24ce2c033648bdb1137bcf8aa32455
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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