3-Phenylprop-2-Enal → 3-Phenylprop-2-En-1-Ol

HRID 1680098Notes

Reaction equation

HRID 1680098 reaction equation
C(B)(C(C)C)(C)C.C1COCC1.[CH:13](=[O:22])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH2:13]([OH:22])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 3073-Phenylprop-2-EnalHCID 178419184HCID 178419184, compound

Product 1

HCID 3083-Phenylprop-2-En-1-OlYield 70%

Procedure

The reduction of aldehydes and ketones with TBDA to the corresponding alcohol proceeds at rates comparable to those of thexylborane-THF. Cinnamaldehyde may be completely reduced by excess TBDA, but treatment with 1 molar equivalent at 0° C. for 15 minutes produces cinnamyl alcohol (70% yield) as the sole product. Similarly, only the aldehyde group of campholenic aldehyde is reduced to give the corresponding alcohol in 80% isolated yield.

Sources & evidence

ORD record
ord-5b147450b0f44342b42b05ff3e5b437c
Source dataset
uspto-grants-1981_06
Patent number
US04271317

Reaction notes

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