Acetic Acid → HCID 11138055, compound

HRID 651270Notes

Reaction equation

[C:1](O)(=O)[CH3:2].[C:5](O)(=O)[CH2:6]C.[Cl:10][CH:11]([Cl:15])[C:12]([OH:14])=[O:13].[CH:16](O)=O>>[Cl:10][CH:11]([Cl:15])[C:12]([O:14][CH2:5][CH:6]=[C:1]([CH3:2])[CH3:16])=[O:13]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 284Formic Acid

HCID 1032Propionic Acid

HCID 6597Dichloroacetic Acid

Product 1

HCID 11138055HCID 11138055, compound

Procedure

This reaction fails for acetic acid (Ka=1.75×10−5), propionic acid (Ka=1.34×10−5), et al., and is even quite slow when one uses formic acid (Ka=1.77×10−4). In contrast, the use of dichloroacetic acid (Ka=5.53×10−2) in molar excess in the above reaction results in a moderate yield of the corresponding prenyl ester (7), prenyl dichloroacetate. Once the ester (7) is obtained, it can be readily saponified using sodium carbonate, sodium hydroxide, potassium carbonate et al., in aqueous alcohol at room temperature to yield prenyl alcohol (2).

Sources & evidence

ORD record: ord-e0132dad43914995bb925e31281396b5
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06278016B1

Reaction notes

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