HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Methoxybenzyl alcohol → 5-HYDROXYPHTHALIDE
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Methoxybenzyl alcohol | HCID 81437 | — |
| Reactant | 5-methoxy-3H-isobenzofuran-1-one | HCID 10535012 | — |
| Reactant | 7-methoxy-3H-isobenzofuran-1-one | HCID 10986583 | — |
| Product | 5-HYDROXYPHTHALIDE | HCID 231886 | — |
Reaction Steps
The reactions are also highly stereo- and regiospecific. Thus, thallation-carbonylation of cis- and trans-2-phenylcyclohexanoles (examples 7 and 8) provide exclusively the cis and trans fused tricyclic lactones respectively. Substituents on the aromatic ring are also observed to effect a very pronounced directive effect. For example, thallation-carbonylation of m-methoxybenzyl alcohol affords the 5-methoxyphthalide in 89% yield and only a trace of the 7-methoxyphthalide (example 4). Similarly, m-hydroxybenzyl alcohol affords a 95% isolated yield of pure 5-hydroxyphthalide (example 5).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04279823 |
| Source dataset | uspto-grants-1981_07 |
| ORD ID | ord-79eb56718e6a44f9b2d722b2fe748742 |
| Source note | uspto-grants-1981_07 |