Methanol → 2-Benzyl-4-hydroxy-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

HRID 1177223Notes

Reaction equation

HRID 1177223 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([OH:10])[C:7]([CH2:11]/[CH:12]=[CH:13]/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]([OH:20])[CH:5]=1.CO>Cl>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([OH:10])[C:7]2[CH2:11][CH:12]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[O:20][C:6]=2[CH:5]=1)=[O:21]

Participants

4

Reactant 2

HCID 887MethanolHCID 581462273,5-Dihydroxy-4-((E)-3-phenyl-allyl)-benzoic acid methyl ester

Product 1

HCID 595601152-Benzyl-4-hydroxy-2,3-dihydro-benzofuran-6-carboxylic acid methyl esterYield 76.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3,5-dihydroxy-4-((E)-3-phenyl-allyl)-benzoic acid methyl ester (220 h) (12 g, 0.032 mol) in HCl (g)/MeOH (4 N, 150 mL) was stirred at room temperature for 2 days. The reaction solution was concentrated to give a brown solid. The crude solid was re-crystallized from EtOAc to give the product (7 g) as a yellow solid. The mother liquid was concentrated to give a brown solid (5 g). The total yield is 98%. 1H NMR (400 MHz, CDCl3): δ 9.90 (br, 1H), 7.27˜7.46 (m, 5H), 7.00 (s, 1H), 6.87 (s, 1H), 5.07 (d, 1H), 3.78 (s, 3H), 2.65 (d, 2H), 2.16 (m, 1H), 1.92 (m, 1H).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customto give a brown solid
  3. customThe crude solid was re-crystallized from EtOAc

Sources & evidence

ORD record
ord-a56939dc104f4f4c8592942ffa367507
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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