HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butyl (2E)-3-{4-[cyclooctylidene(4-hydroxyphenyl)methyl]phenyl}prop-2-enoate → (2E)-3-{4-[Cyclooctylidene(4-hydroxyphenyl)methyl]phenyl}prop-2-enoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-Butyl (2E)-3-{4-[cyclooctylidene(4-hydroxyphenyl)methyl]phenyl}prop-2-enoate | HCID 86613506 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Product | (2E)-3-{4-[Cyclooctylidene(4-hydroxyphenyl)methyl]phenyl}prop-2-enoic acid | HCID 11210670 | 25.6% |
Reaction Steps
tert-Butyl (2E)-3-{4-[cyclooctylidene(4-hydroxyphenyl)methyl]phenyl}prop-2-enoate (50) (0.0586 g, 0.140 mmole) was dissolved in methylene chloride (1 mL) and trifluoroacetic acid (1 mL). The solution was stirred at RT for 4 h, then was concentrated. The residue was recrystallized from EtOAc to provide compound 51 (0.013 g, 25%) as a white solid. 1H NMR (DMSO-d6): δ 12.32 (s, 1H), 9.27 (s, 1H), 7.58 (d, J=8.1 Hz, 2H), 7.51 (d, J=16.1 Hz, 1H), 7.14 (d, J=8.1 Hz, 2H), 6.92 (d, J=8.4 Hz, 2H), 6.66 (d, J=8.4 Hz, 2H), 6.43 (d, J=16.1 Hz, 1H), 2.18 (m, 4H), 1.59 (m, 2H), 1.45 (m, 8H). LRMS (ESI): m/z 361 (M−H)−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07799828B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-478705ebd0a240f89635129dc8929630 |
| Source note | uspto-grants-2010_09 |