Methanol → methyl (3R)-2-methyl-3-hydroxypentanoate

HRID 1900317Notes

Reaction equation

HRID 1900317 reaction equation
[CH3:1][CH:2]([C@H:7]([O:10]C(=O)CCCCCCCCCCC)[CH2:8][CH3:9])[C:3]([O:5][CH3:6])=[O:4].CO.S(=O)(=O)(O)O>O>[CH3:1][CH:2]([C@H:7]([OH:10])[CH2:8][CH3:9])[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 54352518HCID 54352518, compound

Product 1

HCID 53772632methyl (3R)-2-methyl-3-hydroxypentanoateYield 38.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.5 g of methyl (3R)-2-methyl-3-dodecanoyloxypentanoate, 12 ml of methanol and 0.5 ml of concentrated sulfuric acid was refluxed for 8 hours, and 20 ml of water was added thereto followed by ether extraction. The ether phase was dried over anhydrous sodium sulfate and ether was distilled away, and then the residue was distilled to give 0.6 g of methyl (3R)-2-methyl-3-hydroxypentanoate of the following formula, b.p. 52.5° C. (2.5 mm Hg), [α]D30 =-10.7°(C=0.61, CHCl3). ##STR84##

Workup

  1. temperaturewas refluxed for 8 hours
  2. extractionthereto followed by ether extraction
  3. dry with materialThe ether phase was dried over anhydrous sodium sulfate and ether
  4. distillationwas distilled away
  5. distillationthe residue was distilled

Sources & evidence

ORD record
ord-ded3a6a72ec64bcd9260dc2226d00525
Source dataset
uspto-grants-1996_11
Patent number
US05574182

Reaction notes

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