Toluene → 4-Hydroxy-3-propoxybenzaldehyde

HRID 987870Notes

Reaction equation

HRID 987870 reaction equation
CC1(C)CO[CH:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([O:15][CH2:16][CH2:17][CH3:18])[CH:9]=2)[O:4]C1.C1(C)C=CC=CC=1>C(O)=O>[OH:14][C:11]1[CH:12]=[CH:13][C:8]([CH:5]=[O:4])=[CH:9][C:10]=1[O:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 1140TolueneHCID 22987076HCID 22987076, compound

Product 1

HCID 17126234-Hydroxy-3-propoxybenzaldehydeYield 0.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 1.26 g (4.74 mmol) of 4-(5,5-dimethyl-1,3-dioxan-2-yl)-2-propoxyphenol, 20 ml of toluene and 20 ml of formic acid was vigorously stirred for 2 hours at room temperature. Thereafter, the reaction mixture was partitioned between toluene and water and the organic phase was washed several times with water, dried over magnesium sulfate, filtered and evaporated down. Crystallization of the residue from a mixture of 10 ml of diethyl ether and 20 ml of hexane gave 0.78 mg of 4-hydroxy-3-propoxybenzaldehyde.

Workup

  1. customThereafter, the reaction mixture was partitioned between toluene and water
  2. washthe organic phase was washed several times with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated down
  6. customCrystallization of the residue
  7. additionfrom a mixture of 10 ml of diethyl ether and 20 ml of hexane

Sources & evidence

ORD record
ord-22979cd9413c4b5fa6b09df8a67e6f1c
Source dataset
uspto-grants-2003_10
Patent number
US06632909B2

Reaction notes

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