Hydrochloric Acid → 4-Allyl-3,5-dihydroxy-benzoic acid methyl ester

HRID 1177081Notes

Reaction equation

HRID 1177081 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([O:10]COC)[C:7]([CH2:14][CH:15]=[CH2:16])=[C:6]([O:17]COC)[CH:5]=1.Cl>CO>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:5]=[C:6]([OH:17])[C:7]([CH2:14][CH:15]=[CH2:16])=[C:8]([OH:10])[CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59560396Methyl 4-allyl-3,5-bis(methoxymethoxy)benzoate

Product 1

HCID 537917924-Allyl-3,5-dihydroxy-benzoic acid methyl esterYield 79.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-allyl-3,5-bis-methoxymethoxy-benzoic acid methyl ester (10a) (513 mg, 1.73 mmol) in MeOH (4 mL) was added 4N HCl (4 mL). The reaction mixture was stirred at room temperature overnight. The mixture was quenched with H2O (80 mL) and extracted with EtOAc (2×80 mL). The organic layers were dried over MgSO4 and concentrated to give yellow oil which was purified by flash column chromatography eluting with 15-25% EtOAc in hexanes to give a pale yellow solid (285 mg, 79% yield). 1H NMR (400 MHz, CDCl3) δ 7.20 (s, 2 H) 5.95-6.06 (m, J=5.31, 5.31 Hz, 1 H) 5.76-5.82 (m, 2 H) 5.15-5.20 (m, 1 H) 5.12-5.15 (m, 1 H) 3.90 (s, 3 H) 3.50-3.55 (m, 2 H); LCMS for C11H12O4S m/z 209.10 (M+H+).

Workup

  1. customThe mixture was quenched with H2O (80 mL)
  2. extractionextracted with EtOAc (2×80 mL)
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customto give yellow oil which
  6. customwas purified by flash column chromatography
  7. washeluting with 15-25% EtOAc in hexanes

Sources & evidence

ORD record
ord-aecd7b6527c84561a08e111c00e2ca41
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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