HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Allyl-3,5-dihydroxy-benzoic acid methyl ester → 4-Hydroxy-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Allyl-3,5-dihydroxy-benzoic acid methyl ester | HCID 53791792 | — |
| Reactant | 6-Methoxy-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester | HCID 54389757 | — |
| Catalyst | Zirconium chloride (ZrCl4), (T-4)- | HCID 9856075 | — |
| Product | 4-Hydroxy-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester | HCID 59560056 | — |
Reaction Steps
The title compound was prepared in a similar manner as described for Intermediate 1d, from zirconium(IV) chloride and 4-allyl-3,5-dihydroxy-benzoic acid methyl ester (10b) (85 mg, 0.41 mmol). Purification by flash column chromatography eluting with 15-25% EtOAc in hexane gave a pale yellow solid (58 mg, 68% yield). 1H NMR (400 MHz, CDCl3) δ 7.17-7.21 (m, 2 H) 5.76 (s, 1 H) 4.42-4.51 (m, 1H) 3.91 (s, 3 H) 3.11-3.21 (m, 2 H) 1.60 (d, J=6.57 Hz, 3 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08119624B2 |
| Source dataset | uspto-grants-2012_02 |
| ORD ID | ord-1efb6d4d54904c30a05e06b9f2b926f3 |
| Source note | uspto-grants-2012_02 |