Water → 6,7-Dimethoxy-3,4-dihydronaphthalene-2-carbaldehyde

HRID 2175705Notes

Reaction equation

HRID 2175705 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9](O)[CH2:8][CH2:7][CH2:6]2.P(Cl)(Cl)(Cl)=O.[C:21]([O-])(=[O:23])C.[Na+].O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([CH:21]=[O:23])[CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 627354556,7-Dimethoxy-1,2,3,4-tetrahydronaphthalen-1-ol

Product 1

HCID 129383346,7-Dimethoxy-3,4-dihydronaphthalene-2-carbaldehydeYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-1-ol (208 mg, 1 mmol) in dry DMF (5 mL) was cooled in an ice bath and phosphoryl chloride (0.2 mL, 2.3 mmol) was added dropwise. The reaction mixture was heated at 90° C. for 3 hours, then cooled and treated with a cold saturated aqueous solution of sodium acetate (2 mL) and stirred at room temperature for 10 min. Water was added and the mixture was extracted with DCM. The combined organic phase was washed with brine and dried over sodium sulfate. The solvent was then removed under reduced pressure to afford 6,7-dimethoxy-3,4-dihydronaphthalene-2-carbaldehyde as white solid (160 mg, 46%). LC-MS (ES-API); rt 8.23 min; m/z calculated for C13H14O3 [M+H]+ 219.1, found 219.0.

Workup

  1. temperaturecooled
  2. extractionthe mixture was extracted with DCM
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-b59c0bbb82454e7c9cf4bfc3f5720ce1
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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