Acetic Acid → HCID 19095306, compound

HRID 486543Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:20][CH3:21])[CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([Cl:15])=[CH:10][CH:11]=2)[C:6]1=NN(C)C.[O-:22]I(=O)(=O)=O.[Na+].C([O-])(=O)C.[Na+].C(O)(=O)C>O1CCCC1.O>[CH3:1][O:2][CH:3]([O:20][CH3:21])[CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([Cl:15])=[CH:10][CH:11]=2)[C:6]1=[O:22]

Participants

Conditions

Temperature: 50 °C

Procedure

7-Chloro-1-(dimethylhydrazono)-1,2,3,4-tetrahydro-2-naphthaleneacetaldehyde dimethyl acetal (16.0 g) was dissolved under argon in 700 ml of tetrahydrofuran and 180 ml of water. The solution was treated in succession with 30.8 g of sodium (meta)periodate, 11.8 g of sodium acetate and 120 ml of acetic acid and stirred at 50° C. for 18 hours. Subsequently, 2000 ml of water were added and the mixture was extracted three times with 500 ml of ethyl acetate each time. The organic phases were washed with 500 ml of a saturated sodium chloride solution, combined, dried over MgSO4 and freed from solvent. The crude product, 18.4 g of dark brown oil, was chromatographed on 500 g of silica gel with ethyl acetate/hexane (1:3) as the eluent. There were obtained 4.8 g (35%) of 7-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetaldehyde dimethyl acetal.

Workup

extractionthe mixture was extracted three times with 500 ml of ethyl acetate each time
washThe organic phases were washed with 500 ml of a saturated sodium chloride solution
dry with materialdried over MgSO4
customThe crude product, 18.4 g of dark brown oil, was chromatographed on 500 g of silica gel with ethyl acetate/hexane (1:3) as the eluent

Sources & evidence

ORD record: ord-b1fb7b8a2f1f49268cc4db9bd1a7990c
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05292732

Reaction notes

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