Hydrochloric Acid → 4-(Benzyloxy)-2-methylbenzoic acid

HRID 1887539Notes

Reaction equation

HRID 1887539 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([CH3:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P([O-])(O)(O)=[O:19].[Na+].S(=O)(=O)(O)N.Cl([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+].Cl>O1CCOCC1.O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]([OH:19])=[O:14])=[C:11]([CH3:17])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 5987Sulfamic AcidHCID 24437Sodium SulfiteHCID 27598062-Methyl 4-benzyloxybenzaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 211943914-(Benzyloxy)-2-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
10 °C

Procedure

A solution of 4-benzyloxy-2-methylbenzaldehyde (20 g) in 1,4-dioxane (300 mL) was mixed with sodium dihydrogen phosphate (42.4 g) and sulfamic acid (13.7 g) and, while cooling, a solution of sodium chlorite (11.2 g) in water (200 mL) was added in such a way that the temperature did not rise above 10° C. After 20 minutes, sodium sulfite (14.5 g) was added, and the mixture was stirred at 10° C. for a further 15 minutes. The reaction mixture was acidified with hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated.

Workup

  1. temperaturewhile cooling
  2. customdid not rise above 10° C
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-76fec648d5cf4ff5b17bd761bc901a64
Source dataset
uspto-grants-2013_08
Patent number
US08501771B2

Reaction notes

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