Hydrochloric Acid → 4-Butoxy-2-methoxybenzoic acid

HRID 2426740Notes

Reaction equation

HRID 2426740 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1.Br[CH2:13][CH2:14][CH2:15][CH3:16].P([O-])(O)(O)=[O:18].[Na+].S(=O)(=O)(O)O.Cl([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+].Cl>O1CCOCC1.O>[CH2:13]([O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([OH:18])=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1)[CH2:14][CH2:15][CH3:16]

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 8002Butyl bromideHCID 24437Sodium SulfiteHCID 5195414-Hydroxy-2-MethoxybenzaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 64834054-Butoxy-2-methoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
10 °C

Procedure

4-Hydroxy-2-methoxybenzaldehyde was alkylated with 1-bromobutane by method H. The resulting aldehyde (6.4 g) in dioxane (100 ml) was mixed with sodium dihydrogen phosphate (14.4 g) and sulfuric acid (2.4 ml), and the solution was cooled to 10° C. A solution of sodium chlorite (3.61 g) in water (100 ml) was added in such a way that the temperature did not exceed 10° C. 15 minutes after the addition was complete, sodium sulfite (4.6 g) was added. After a further 15 minutes, the pH was adjusted to 2 with hydrochloric acid and the dioxane was removed in a rotary evaporator. The aqueous phase was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative HPLC. This resulted in the product with the molecular weight of 224.26 (C12H16O4); MS (ESI): 225 (M+H+).

Workup

  1. customdid not exceed 10° C
  2. addition15 minutes after the addition
  3. customthe dioxane was removed in a rotary evaporator
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by preparative HPLC
  9. customThis resulted in the product with the molecular weight of 224.26 (C12H16O4)

Sources & evidence

ORD record
ord-53a1d7a06c184d779d6173c63440cf31
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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