Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Isophthalaldehyde | HCID 34777 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-(Hydroxymethyl)benzaldehyde | HCID 13131455 | 40.1% |
Reaction Steps
Isophthalaldehyde (150 g, 1.1 mole) was dissolved in THF (1 L) and EtOH (1 L) at 0° C. NaBH4 (11.0 g, 291 mmol) was added portionwise and the mixture stirred 1 hour at 0° C. Addition of 25% aq. NH4OAc and extraction with EtOAc (2×) followed by purification by flash chromatography (20% to 40% EtOAc in hexanes) yielded 60 g of 3-(hydroxymethyl)benzaldehyde.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05350760 |
|---|
| Source dataset | uspto-grants-1994_09 |
|---|
| ORD ID | ord-318786cf659b40c092e8823e2707220a |
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| Source note | uspto-grants-1994_09 |
|---|
