3-Hydroxybenzaldehyde → 3-Propoxybenzaldehyde

HRID 1953189Notes

Reaction equation

HRID 1953189 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7](/[CH:11]=C/C(Cl)=O)[CH:8]=[CH:9][CH:10]=1)[CH2:2][CH3:3].[OH:16]C1C=C(C=CC=1)C=O.ICCC>>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[CH:11]=[O:16])[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 1013-Hydroxybenzaldehyde2×HCID 336431-IodopropaneHCID 18434037HCID 18434037, compound

Product 1

HCID 27604693-Propoxybenzaldehyde

Procedure

For example, (E)-3-(3'-propyloxyphenyl)-2-propenoyl chloride, used in Example 3 (i), can be prepared from commercially available 3-hydroxybenzaldehyde by reacting 3-hydroxybenzaldehyde with 1-iodopropane to give 3-propyloxy benzaldehyde. 3-Propyloxy benzaldehyde is then reacted with malonic acid to give the corresponding propenonic acid which is subsequently converted into (E)-3-(3'-propyloxyphenyl)-2-propenoyl chloride by reaction with oxalyl chloride.

Sources & evidence

ORD record
ord-a468ab6c65814f588d99029a71621843
Source dataset
uspto-grants-2000_09
Patent number
US06114549

Reaction notes

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