Sodium Bicarbonate → 1-Acetyloxy-2-(3-Methoxyphenyl)-6-Methoxy-3,4-Dihydronaphthalene

HRID 1357669Notes

Reaction equation

HRID 1357669 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=3)[C:10]2=[O:21])[CH:6]=[CH:7][CH:8]=1.O.[C:23]1([CH3:33])C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=[O:35].[Na+]>C(CC([O-])=O)(C)=C>[C:23]([O:21][C:10]1[C:11]2[C:16](=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=2)[CH2:17][CH2:18][C:9]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:35])[CH3:33]

Participants

5

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 129722052-(3-Methoxyphenyl)-6-methoxy-1-tetralone

Product 1

HCID 129722061-Acetyloxy-2-(3-Methoxyphenyl)-6-Methoxy-3,4-Dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 18355900IsopropenylacetateSolvent

Procedure

A suspension was prepared of 47 g (167 mmol) of 2-(3-methoxyphenyl)-6-methoxy-1-tetralone and 4.7 g of p-toluenesulfonic acid mono-hydrate in 470 mL of iso-propenylacetate. The reaction mixture was refluxed for forty-eight hours under a nitrogen atmosphere. The reaction was allowed to cool and 10 g of NaHCO3 was added, the solution was poured into 500 mL of an aqueous solution of NaHCO3. The aqueous solution was extracted three times with 200 mL portions of EtOAc. The combined organic extract was washed with brine, dried with Na2SO4, and evaporated to a dark oil. This yielded 52.7 g of the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for forty-eight hours under a nitrogen atmosphere
  2. temperatureto cool
  3. extractionThe aqueous solution was extracted three times with 200 mL portions of EtOAc
  4. extractionThe combined organic extract
  5. washwas washed with brine
  6. dry with materialdried with Na2SO4
  7. customevaporated to a dark oil

Sources & evidence

ORD record
ord-2dbb6c5ef8034afabd1f24261ffbe468
Source dataset
uspto-grants-2003_07
Patent number
US06593345B1

Reaction notes

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