HuagongsheHuagongshe Chemistry Print Report · For research reference only
Piperonyl alcohol → HCID 66906062, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Piperonyl alcohol | HCID 10322 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | Dimethyl 3-hydroxyphthalate | HCID 12223651 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66906062 | HCID 66906062 | 102.9% |
Reaction Steps
To a stirred suspension of 3-hydroxyphthalic acid dimethyl ester (1.0 g, 4.8 mmol), benzo[1,3]dioxol-5-yl-methanol (1.4 g, 9.5 mmol), and polymer-supported triphenyl phosphine (3.0 g, 9.5 mmol) in THF (30 mL) in an ice-bath was slowly added diisopropyl azodicarboxylate (1.9 mL, 9.5 mmol) and stirred at r.t. overnight. The mixture was filtered and the filter was washed with ethyl acetate (10 mL). The filtrate was evaporated and the residue was purified by flash column chromatography (EtOAc/Hexane) to give 3-(benzo[1,3]dioxol-5-ylmethoxy)-phthalic acid dimethyl ester (1.7 g, 102% crude yield). The product was used in the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09181216B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-ad21aeaf2f4646e68143e0d144702526 |
| Source note | uspto-grants-2015_11 |