HCID 54518938, compound → Ethyl (2R)-2,3-dihydroxy-2-methylpropanoate

HRID 224731Notes

Reaction equation

HRID 224731 reaction equation
C([O:8][C@:9]([CH3:17])([CH2:15][OH:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[OH:8][C@:9]([CH3:17])([CH2:15][OH:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 54518938HCID 54518938, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 53737198Ethyl (2R)-2,3-dihydroxy-2-methylpropanoateYield 92.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

22 g of ethyl (R)-2-benzyloxy-3-hydroxy-2-methyl-propionate (manufactured in accordance with Example 1) in 150 ml of ethyl acetate were hydrogenated with hydrogen gas in the presence of 11 g of 5% by weight palladium/carbon catalyst up to the cessation of the hydrogen uptake. The catalyst was filtered off, washed with ethyl acetate (2×50 ml), the filtrate was concentrated in the vacuum and the residual oil was distilled at 56°-57°/0.1 mmHg. There were obtained 12.7 g of ethyl (R)-2,3-dihydroxy-2-methyl-propionate in the form of a colorless viscous liquid. [α]D =+0.339° (undiluted);=+11.6° (c=2.12 in chloroform).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate (2×50 ml)
  3. concentrationthe filtrate was concentrated in the vacuum
  4. distillationthe residual oil was distilled at 56°-57°/0.1 mmHg

Sources & evidence

ORD record
ord-00253f1f3bf749db9dd323445dcc9b6b
Source dataset
uspto-grants-1980_11
Patent number
US04234490

Reaction notes

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