2,3-Dihydroxybutanedioic Acid → HCID 54555247, compound

HRID 2049856Notes

Reaction equation

HRID 2049856 reaction equation
[CH3:1][CH:2]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:3][CH:4]=[CH:5][C:6](=[O:8])[CH3:7].O.[BH4-].[Na+].C(O)(=O)C(C(C(O)=O)O)O>CCOCC.C(O)C>[CH3:1][CH:2]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:3][CH:4]=[CH:5][CH:6]([OH:8])[CH3:7]

Participants

7

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 54414003HCID 54414003, compound

Product 1

HCID 54555247HCID 54555247, compoundYield 494.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

58, 9 g of 6,8-dimethyl-3-nonen-2-one, 25 ml of water and 70 ml of ethanol are added to a 250 ml round flask which is provided with a stirrer and a thermometer. 8 g of sodium borohydride are added slowly while maintaining the temperature below 25° C. by cooling with a cold water bath. The mixture is now stirred at 25° C. for 3 hours. 50 ml of a saturated solution of tartaric acid and 100 ml of ether are added to the reaction mixture. The organic layer is then washed with brine until neutral. The solvent is evaporated. There are obtained 58 g of crude product, distillation of which yields 45 g (76,2%) of 6,8-dimethyl-3-nonen-2-ol of boiling point 88°-90° C./5 mm; nD20 =1,4435; d420 =0,8330.

Workup

  1. customis provided with a stirrer
  2. temperaturewhile maintaining the temperature below 25° C.
  3. temperatureby cooling with a cold water bath
  4. washThe organic layer is then washed with brine until neutral
  5. customThe solvent is evaporated
  6. customThere are obtained
  7. distillation58 g of crude product, distillation of which

Sources & evidence

ORD record
ord-1f216f9e4f0f484c91de520e48c5eb99
Source dataset
uspto-grants-1980_04
Patent number
US04198532

Reaction notes

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