Water → Methyl 7-hydroxy-2-(4-methoxyphenyl)-1,3-benzodioxole-5-carboxylate

HRID 1471416Notes

Reaction equation

HRID 1471416 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.CO[CH:16](OC)[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.O>C1(C)C=CC=CC=1.ClCCl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:9][C:8]1[C:6]2[O:7][CH:16]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[O:5][C:4]=2[CH:3]=[C:2]([C:1]([O:12][CH3:13])=[O:11])[CH:10]=1

Participants

7

Reactant 3

HCID 962WaterHCID 7428Methyl GallateHCID 75140p-(Dimethoxymethyl)anisole

Product 1

HCID 11415398Methyl 7-hydroxy-2-(4-methoxyphenyl)-1,3-benzodioxole-5-carboxylateYield 52.4%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of methyl gallate (10 g, 54.3 mmol) in toluene (25 ml), p-toluensulfonic acid (29 mg) and p-anisaldehyde dimethylacetal (11.56 ml, 67.88 mmol) were added. The reaction was refluxed for 1.5 hours with continuous removal of water. The mixture was diluted with dichloromethane (70 ml) and washed with a saturated aqueous NaHCO3 solution (100 ml) and extracted with ethyl acetate (3×50 ml) The organic layer was washed with water (100 ml), dried over sodium sulphate and concentrated under reduced pressure. The residue was crystallized by n-hexane. The product (8.6 g) was obtained.

Workup

  1. additionwere added
  2. washwashed with a saturated aqueous NaHCO3 solution (100 ml)
  3. extractionextracted with ethyl acetate (3×50 ml) The organic layer
  4. washwas washed with water (100 ml)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized by n-hexane

Sources & evidence

ORD record
ord-38fef4d14d5447fc83237edc6743be53
Source dataset
uspto-grants-2015_04
Patent number
US09012435B2

Reaction notes

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