Hydrochloric Acid → 4-(5-Phenylpentyloxy)-3-methoxy-benzaldehyde

HRID 378975Notes

Reaction equation

HRID 378975 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C([O-])([O-])=O.[Na+].[Na+].[C:18]1([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]OS(C)(=O)=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>CN(C)C=O>[C:18]1([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:9][C:8]2[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=2[O:6][CH3:7])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1183VanillinHCID 10340Sodium CarbonateHCID 116301071-Methylsulfonyloxy-5-phenylpentane

Product 1

HCID 216972874-(5-Phenylpentyloxy)-3-methoxy-benzaldehydeYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of vanillin (12.49 g, 82.1 mmoles) in dimethylformamide was added with Na2CO3 (17.4 g, 164 mmoles) and KI (catalytic amount). The mixture was brought to 90° C. then slowly added with methansulfonic acid 5-phenyl-pentyl ester (24.87 g, 103 mmoles) obtained as described in example 11, in dimethylformamide (40 ml). After 1.5 hours the mixture was poured into 1N HCl and thrice extracted with pentane, anhydrified and dried. The residue was purified by silica gel flash chromatography (eluent: petrolatum/ethyl acetate 9:1), so 7.46 g of the title product were obtained (yield: 97%).

Workup

  1. customwas brought to 90° C.
  2. customobtained
  3. extractionextracted with pentane
  4. customdried
  5. customThe residue was purified by silica gel flash chromatography (eluent: petrolatum/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-d62ea3f5e5cb47a1a1f930c52d2b8cac
Source dataset
uspto-grants-2001_10
Patent number
US06297257B1

Reaction notes

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