Formic Acid → (E)-3-formylbut-2-enyl acetate

HRID 894852Notes

Reaction equation

HRID 894852 reaction equation
C([O:4][CH:5](OC(=O)C)[C:6]([CH3:13])=[CH:7][CH2:8][O:9][C:10](=[O:12])[CH3:11])(=O)C.C(O)=O>O>[C:10]([O:9][CH2:8]/[CH:7]=[C:6](\[CH3:13])/[CH:5]=[O:4])(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 284Formic Acid2×HCID 538659791,1,4-Triacetoxy-2-methyl-2-butene

Product 1

HCID 6365337(E)-3-formylbut-2-enyl acetateYield 75.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

48.8 parts of 1,1,4-triacetoxy-2-methyl-but-2-ene, having the isomer composition stated in Example 1, 400 parts of formic acid and 10.8 parts of water are boiled for 3 hours. After stripping off the formic acid and water on a rotary evaporator, fractional distillation of the residue gives 21.5 parts of 4-acetoxy-2-methylcrotonaldehyde (75.6% of theory) of boiling point 102°-105° C./21 mbar (nD20 =1.4642). According to NMR analysis, the aldehyde obtained consists of 98.3% (E)- and 1.7% (Z)-4-acetoxy-2-methylcrotonaldehyde.

Workup

  1. customon a rotary evaporator, fractional distillation of the residue

Sources & evidence

ORD record
ord-ed72298fbd5042bb829e2e162445eb04
Source dataset
uspto-grants-1981_08
Patent number
US04284796

Reaction notes

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