Water → HCID 131719641, compound

HRID 1900314Notes

Reaction equation

HRID 1900314 reaction equation
[CH2:1]([CH:4]([C@H:12]([O:14]C(=O)CCCCCCCCCCC)[CH3:13])[C:5]([O:7][C:8](C)(C)C)=[O:6])[CH2:2][CH3:3].S(=O)(=O)(O)O.O>CO>[CH2:1]([CH:4]([C@H:12]([OH:14])[CH3:13])[C:5]([O:7][CH3:8])=[O:6])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 131719642HCID 131719642, compound

Product 1

HCID 131719641HCID 131719641, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4.5 g of t-butyl (3R)-2-propyl-3-dodecanoyloxybutanoate obtained in (1) above 45 ml of methanol and 0.5 ml of concentrated sulfuric acid was refluxed for 40 hours and 50 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 the residue was distilled and 1.2 g of methyl (3R)-2-propyl-3-hydroxybutanoate of the following formula was obtained. b.p. 76°-81° C. (5.0 mm Hg), [α]D26 =2.9°(C-1.37, CHCl3) ##STR79##

Workup

  1. extractionthereto followed by ether extraction
  2. dry with materialThe ether phase was dried over anhydrous sodium sulfate, and ether
  3. distillationwas distilled away
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-186d37946b67442fab53b788ca948824
Source dataset
uspto-grants-1996_11
Patent number
US05574182

Reaction notes

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