Acetic Acid → Ethyl 3,4-dihydro-1-methyl-2-naphthaleneacetate

HRID 1719561Notes

Reaction equation

HRID 1719561 reaction equation
[H-].[Na+].[CH3:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][C:5]1=O.[C:15]([OH:18])(=[O:17])[CH3:16].[CH2:19]([CH2:22]OC)OC>>[CH3:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][C:5]=1[CH2:16][C:15]([O:18][CH2:19][CH3:22])=[O:17]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 80711,2-Dimethoxyethane3×HCID 24758Sodium hydrideHCID 982091-Methyl-3,4-dihydro-1H-naphthalen-2-one

Product 1

HCID 13815996Ethyl 3,4-dihydro-1-methyl-2-naphthaleneacetate

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 24 g (0.5 mole) of sodium hydride (50% in oil dispersion) in 750 ml of dimethoxyethane, cooled to 0° C., was added dropwise over a one hour period a solution of 112.1 g (0.5 mole) of triethyl phosphonoacetate [(C2H5)2OP(O)CH2CO2C2H5 ] in 140 ml of dimethoxyethane. The reaction mixture was maintained at about 15° C. during the addition and then stirred at room temperature for two hours. It was then cooled to 5° C. and treated dropwise with a solution of 68.7 g (0.386 mole) of 1-methyl-2-tetralone in 70 ml of dimethoxyethane over a period of one hour. The reaction mixture was stirred overnight, then cooled in an ice bath and acidified with 27 ml of glacial acetic acid. The mixture was poured into ice-water and the layers separated. The aqueous layer was extracted with cyclohexane, and the combined organic layers washed with water and saturated sodium chloride solution. The organic solution was dried over anhydrous magnesium sulfate and concentrated to give 95.8 g of ethyl 3,4-dihydro-1-methyl-2-naphthaleneacetate as a yellow liquid.

Workup

  1. temperatureThe reaction mixture was maintained at about 15° C. during the addition
  2. temperatureIt was then cooled to 5° C.
  3. stirringThe reaction mixture was stirred overnight
  4. temperaturecooled in an ice bath
  5. customthe layers separated
  6. extractionThe aqueous layer was extracted with cyclohexane
  7. washthe combined organic layers washed with water and saturated sodium chloride solution
  8. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d4052365a1f04a8cb10104023658d0fd
Source dataset
uspto-grants-1985_09
Patent number
US04540705

Reaction notes

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