Hydrochloric Acid → p-(Dimethoxymethyl)anisole

HRID 39213

Reaction equation

HRID 39213 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6](C=O)=[CH:7][CH:8]=1.CO[CH:13]([O:16][CH3:17])[O:14][CH3:15].Cl.[OH-].[K+]>CO>[CH3:17][O:16][CH:13]([O:14][CH3:15])[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9005Trimethyl orthoformateHCID 14797Potassium HydroxideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 75140p-(Dimethoxymethyl)anisoleYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
12.5 °C

Procedure

Anisaldehyde (40 g) and trimethylorthoformate (48.25 ml) were added to MeOH (60 ml) at 20-25° C. and the mixture was cooled to 10-15° C. Conc. HCl (0.26 ml) was then added to the mixture at 10-15° C. and was warmed to 20-25° C. followed by stirring at the same temperature for 16-18 hours. 5% aqueous KOH (40 ml) was added to the reaction mixture at 20-25° C. in 10 min and further stirred for 10 minutes. The reaction mixture was extracted with hexane (2×200 ml) and the combined organic layer was washed with DM water (200 ml). The organic layer was concentrated below 40° C. to obtain title compound (51.0 g, 95.2%).

Workup

  1. temperaturewas warmed to 20-25° C.
  2. stirringfurther stirred for 10 minutes
  3. extractionThe reaction mixture was extracted with hexane (2×200 ml)
  4. washthe combined organic layer was washed with DM water (200 ml)
  5. concentrationThe organic layer was concentrated below 40° C.

Sources & evidence

ORD record
ord-5ff95af0f63e4a8ea35a299468d96f9b
Source dataset
uspto-grants-2013_09
Patent number
US08524893B2

Linked notes

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