Methyl 3,4-dimethyl-3-hydroxy-6-heptenoate → HCID 86646154, compound

HRID 551688Notes

Reaction equation

HRID 551688 reaction equation
[CH3:1][C:2]([OH:13])([CH:8]([CH3:12])[CH2:9][CH:10]=[CH2:11])[CH2:3][C:4]([O:6]C)=[O:5]>[OH-].[K+].CO>[CH3:1][C:2]([OH:13])([CH:8]([CH3:12])[CH2:9][CH:10]=[CH2:11])[CH2:3][C:4]([OH:6])=[O:5]

Participants

3

Reactant 1

HCID 86646146Methyl 3,4-dimethyl-3-hydroxy-6-heptenoate

Product 1

HCID 86646154HCID 86646154, compound

Reagents, catalysts & solvents 1

HCID 23689386Potassium hydroxide methanolSolvent

Procedure

Methyl 3,4-dimethyl-3-hydroxy-6-heptenoate (11.7 g, 62.8 mmol) was dissolved in a 2 N potassium hydroxide-methanol solution (44 mL), and the solution was stirred overnight at room temperature. The reaction solution was concentrated, then dissolved in water (30 mL), and washed with ether. The aqueous layer was made acidic (<pH=2) using aqueous hydrochloric acid, followed by two extractions with ethyl acetate. The ethyl acetate layer was washed with saturated saline, then dried, and then concentrated to obtain the compound of interest as an oil substance (10.1 g, 93%). This compound was used in the next reaction without being purified.

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutiondissolved in water (30 mL)
  3. washwashed with ether
  4. extractionfollowed by two extractions with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated saline
  6. customdried
  7. concentrationconcentrated
  8. customto obtain the compound of interest as an oil substance (10.1 g, 93%)
  9. customThis compound was used in the next reaction
  10. customwithout being purified

Sources & evidence

ORD record
ord-caf95960d0594b07beecafdeb44810d3
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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