Benzaldehyde → 2-Methyl-4-(2,3-epoxypropoxy)benzaldehyde

HRID 325342Notes

Reaction equation

HRID 325342 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[CH3:6][C:7]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].C(=O)C1C=CC=CC=1>[OH-].[Na+]>[CH3:6][C:7]1[CH:14]=[C:13]([O:15][CH2:1][CH:3]2[O:5][CH2:4]2)[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 7835EpichlorohydrinHCID 4581854-Hydroxy-2-methylbenzaldehyde

Product 1

HCID 133020652-Methyl-4-(2,3-epoxypropoxy)benzaldehyde

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 2.5 N 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-4-82,3-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
  5. customto give 8.3 g

Sources & evidence

ORD record
ord-87bd1922658b4af5992ccc184f5a67ac
Source dataset
uspto-grants-1984_04
Patent number
US04440774

Reaction notes

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