Hydrochloric Acid → 5-(2,6-Dichloro-4-methoxymethyl-phenoxy)-2-methoxy-benzoic acid

HRID 1168093Notes

Reaction equation

HRID 1168093 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([CH2:19][O:20][CH3:21])[CH:16]=[C:15]([Cl:22])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:13][CH3:14])=[C:9]([CH:12]=1)[CH:10]=[O:11].CC(=CC)C.Cl[O-:29].[Na+].Cl>C(O)(C)(C)C.O1CCCC1.P([O-])(O)(O)=O.[K+]>[Cl:1][C:2]1[CH:18]=[C:17]([CH2:19][O:20][CH3:21])[CH:16]=[C:15]([Cl:22])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:13][CH3:14])=[C:9]([CH:12]=1)[C:10]([OH:29])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 222856575-(2,6-Dichloro-4-methoxymethyl-phenoxy)-2-methoxy-benzaldehydeHCID 23665760Sodium Hypochlorite

Product 1

HCID 222856525-(2,6-Dichloro-4-methoxymethyl-phenoxy)-2-methoxy-benzoic acidYield 100.7%

Reagents, catalysts & solvents 2

HCID 516951Monobasic potassium phosphateSolventHCID 66775918Tert-butanol tetrahydrofuranSolvent

Procedure

To a solution of the title compound of Step C (228 mg, 0.67 mmol) and 2-methyl-2-butene (2M in tetrahydrofuran, 5 ml, 10.0 mmol) in tert-butanol/tetrahydrofuran (1 ml/3 ml) was added slowly a solution of sodium hypochlorite (543 mg, 6.0 mmol) in potassium dihydrogen phosphate aqueous solution (0.6 M, 8 ml). The reaction mixture was stirred for one hour at room temperature. The mixture was acidified with 1N HCl and extracted with ethyl acetate (3×20 ml). The combined organic extracts were washed with 1N HCl (2×40 ml), brine (40 mL), dried, filtered, and concentrated to afford the title compound (241 mg) as a viscous oil which was used in the next step without further purification. MS (APCl−) Calc: 356.0, found: 355.0 (M−1).

Workup

  1. extractionextracted with ethyl acetate (3×20 ml)
  2. washThe combined organic extracts were washed with 1N HCl (2×40 ml), brine (40 mL)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5a6a973b9ae24a3ab7e690493969c841
Source dataset
uspto-grants-2003_09
Patent number
US06620830B2

Reaction notes

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