Propanoic acid, 2-bromo-2-methyl-, ethyl ester → cis-2-[(6,7-Dihydroxy-5,6,7,8-tetrahydro-1-naphthyl)oxy]-2-methylpropionic acid, ethyl ester

HRID 267556Notes

Reaction equation

HRID 267556 reaction equation
[H-].[Na+].[H][H].[OH:5][CH:6]1[CH:15]([OH:16])[CH2:14][C:13]2[C:12]([OH:17])=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:7]1.Br[C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[OH:5][C@H:6]1[C@@H:15]([OH:16])[CH2:14][C:13]2[C:12]([O:17][C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:7]1

Participants

6

Reactant 4

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 24758Sodium hydrideHCID 5955795,6,7,8-Tetrahydronaphthalene-1,6,7-triolHCID 178418361HCID 178418361, compound

Product 1

HCID 86733119cis-2-[(6,7-Dihydroxy-5,6,7,8-tetrahydro-1-naphthyl)oxy]-2-methylpropionic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydride, 50% (0.75 mole) is added in portions with stirring to 50 ml. of cooled absolute ethyl alcohol. After the evolution of hydrogen has subsided, 0.075 mole of 6,7-dihydroxy-5,6,7,8-tetrahydro-1-naphthol is added, followed by the dropwise addition of 0.075 mole of ethyl α-bromoisobutyrate. The reaction mixture is refluxed with stirring for 16 hours. The solvent is evaporated in vacuo, the residue taken up in water and extracted with chloroform. The chloroform extract is washed with water, dried and freed of solvent to give the title compound in the form of an oil.

Workup

  1. temperatureThe reaction mixture is refluxed
  2. stirringwith stirring for 16 hours
  3. customThe solvent is evaporated in vacuo
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. washis washed with water
  7. customdried

Sources & evidence

ORD record
ord-21faacffce32479d9fa97493a6251f00
Source dataset
uspto-grants-1976_03
Patent number
US03943149

Reaction notes

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