Ethyl formate → HCID 70386788, compound

HRID 236542Notes

Reaction equation

HRID 236542 reaction equation
C[O-].[Na+].C([O:6][CH2:7][CH3:8])=O.[CH2:9]([C:19]1[CH:28]=C2[C:22]([CH2:23][CH2:24][CH2:25][C:26]2=[O:29])=[CH:21][CH:20]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>C1(C)C=CC=CC=1>[OH:29][CH:26]=[C:25]1[CH2:24][CH2:23][C:22]2[C:8](=[CH:28][C:19]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:20][CH:21]=2)[C:7]1=[O:6]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 10942334Sodium MethoxideHCID 135480317-Decyl-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 70386788HCID 70386788, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of sodium methoxide (5.4 gm, 40.5 moles), ethyl formate (7.4 gm, 100 mmoles) and 100 mL dry toluene was cooled in an ice bath under inert atomosphere nitrogen. A solution of the 7-decyl-tetralone (11.5 gm, 40 mmoles) in 100 mL dry toluene was added with rapid stirring. The ice bath was removed and the reaction was stirred at room temperature for 4 hours. The reaction mixture was treated with 100 mL water and 100 mL 6N HCl. The organic layer was separated and washed twice with 50 mL saturated sodium chloride, dried over anhydrous Na2SO4, filtered and evaporated to remove all the toluene. The oily residue was used for the next reaction without further purification.

Workup

  1. temperaturewas cooled in an ice bath under inert atomosphere nitrogen
  2. customThe ice bath was removed
  3. additionThe reaction mixture was treated with 100 mL water and 100 mL 6N HCl
  4. customThe organic layer was separated
  5. washwashed twice with 50 mL saturated sodium chloride
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customto remove all the toluene
  10. customThe oily residue was used for the next reaction without further purification

Sources & evidence

ORD record
ord-2170fcd023e24b9a8a280e4322dea676
Source dataset
uspto-grants-1987_02
Patent number
US04645744

Reaction notes

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