Hydrochloric Acid → HCID 10654361, compound

HRID 2079240Notes

Reaction equation

HRID 2079240 reaction equation
CC1(C)[O:6][C@H:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:4](=[O:12])[O:3]1.Cl.[Na+].[Cl-]>C1COCC1>[CH3:11][O:10][C:8]([CH2:7][C@@H:5]([OH:6])[C:4]([OH:12])=[O:3])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 10655203Methyl (R)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-YL)acetate

Product 1

HCID 10654361HCID 10654361, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-((R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetate (17.1 g, 90.9 mmol) was stirred in a 1:1 mixture of THF: 1 M HCl (200 mL) for 1 h at room temperature. After addition of NaCl to nearly saturate the aqueous layer, the mixture was extracted with EtOAc, and the extracts were dried over Na2SO4 and concentrated to obtain (R)-3-(methoxycarbonyl)-2-hydroxypropanoic acid as an oil. 1H NMR (400 MHz, CDCl3) δ 4.58-4.55 (m, 1H), 3.75 (s, 3H), 2.98-2.84 (m, 2H) ppm.

Workup

  1. concentrationto nearly saturate the aqueous layer
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialthe extracts were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-689783b034834d6b8b088cf21eaf7656
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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