Methanol → 3,5-Dihydroxy-4-((E)-3-phenyl-allyl)-benzoic acid methyl ester

HRID 1643697Notes

Reaction equation

HRID 1643697 reaction equation
COC[O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:23]COC)[C:13]=1[CH2:14]/[CH:15]=[CH:16]/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:8]([OH:10])=[O:9].OS(O)(=O)=O.[CH3:32]O>>[CH3:32][O:10][C:8](=[O:9])[C:7]1[CH:6]=[C:5]([OH:4])[C:13]([CH2:14]/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:12]([OH:23])[CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 667560413,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzoic acid

Product 1

HCID 581462273,5-Dihydroxy-4-((E)-3-phenyl-allyl)-benzoic acid methyl esterYield 73%

Procedure

To a solution of 3,5-bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzoic acid (220g) (18 g, 0.05 mol) in MeOH (300 mL) was added catalytic amount of conc. H2SO4 (3 mL) in one portion. The mixture was refluxed overnight. The solution was concentrated. The residue was dissolved in CH2Cl2 (75 mL) and washed with sat. NaHCO3 (25 mL). The organic layers were dried and concentrated to give a brown solid (12 g, 73% yield). 1H NMR (400 MHz, CDCl3): δ 9.63 (s, 2H), 7.11˜7.34 (m, 5H), 6.93 (s, 2H), 6.32 (s, 2H), 3.77 (s, 3H), 3.42 (s, 2H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. concentrationThe solution was concentrated
  3. dissolutionThe residue was dissolved in CH2Cl2 (75 mL)
  4. washwashed with sat. NaHCO3 (25 mL)
  5. customThe organic layers were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6dfa7d853e4a4442a6a9ed42508f3495
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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