Epichlorohydrin → 2-Methyl-4-(2,3-epoxypropyl)benzaldehyde

HRID 235923Notes

Reaction equation

HRID 235923 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[CH3:6][C:7]1[CH:14]=[C:13](O)[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10]>[OH-].[Na+]>[CH3:6][C:7]1[CH:14]=[C:13]([CH2:1][CH:3]2[O:5][CH2:4]2)[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 4581854-Hydroxy-2-methylbenzaldehyde

Product 1

HCID 200299172-Methyl-4-(2,3-epoxypropyl)benzaldehydeYield 71.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
55 °C

Procedure

To epichlorohydrin (20 g., 0.216 mole) heated at 55° C. is added dropwise a solution of 2-methyl-4-hydroxybenzaldehyde (9.0 g., 0.066 mole) in 2.5N sodium hydroxide solution (40 ml.). After the addition, the solution is allowed to stir an additional 3 hours at 55° C. and then at room temperature overnight. The oil is distilled to give 8.3 g of 2-methyl-4-(2,3-epoxypropyl)benzaldehyde, m.p. 160°-170° C. at 1 mm. Hg.

Workup

  1. additionAfter the addition
  2. customat room temperature
  3. customovernight
  4. distillationThe oil is distilled

Sources & evidence

ORD record
ord-37cb86dad2664b549ca28236e9aa0d5c
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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