Glycolic Acid → HCID 19018144, compound

HRID 1656727Notes

Reaction equation

HRID 1656727 reaction equation
[OH-].C[N+](C)(C)C.[C:7]([OH:11])(=[O:10])[CH2:8][OH:9].Br[CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15]>CN(C)C=O>[OH:9][CH2:8][C:7](=[O:11])[O:10][CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 757Glycolic AcidHCID 60966Tetramethylammonium hydroxideHCID 95576Methyl 2-bromopropionate

Product 1

HCID 19018144HCID 19018144, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tetramethylammonium hydroxide (25% in methanol) was added to a stirring solution of glycolic acid (3.8 g, 50 mmol) in 5 mL dimethylformamide cooled on ice until a pH of 7 was indicated by moistened pH paper. Methyl 2-bromopropionate (6.1 mL, 55 mmol) was added and the reaction was stirred at room temperature for 5 d. The reaction mixture was filtered, the solids were washed with ethyl ether, and the combined filtrate and ether solution was washed with 5% NaCl/5% NaHCO3. Sufficient ethyl ether was added to effect rapid separation of the phases, the aqueous phase was extracted with CH2Cl2, and the organic phases were combined and dried with MgO4. The solvent was removed and the resulting residue was distilled under reduced pressure to give the title compound: b.p. 64° C./0.05 mm Hg; 1H NMR δ 1.53 (d, 3H, J=7.2 Hz), δ 2.78 (bs, 1H), δ 3.77 (s, 3H),δ 4.24 (d, 1H, J=17.4 Hz) δ 4.31 (d, 1H, J=17.4 Hz), δ 5.22 (q, 1H, J=7.1 Hz), HRMS calcd for C6H9O5Tms (M--CH3) 219.0688, obsd 219.0708.

Workup

  1. temperaturecooled on ice until a pH of 7
  2. filtrationThe reaction mixture was filtered
  3. washthe solids were washed with ethyl ether
  4. washthe combined filtrate and ether solution was washed with 5% NaCl/5% NaHCO3
  5. additionSufficient ethyl ether was added
  6. customseparation of the phases
  7. extractionthe aqueous phase was extracted with CH2Cl2
  8. customdried with MgO4
  9. customThe solvent was removed
  10. distillationthe resulting residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-cc95b13c4e8d40ab99fe698781c7ac55
Source dataset
uspto-grants-1993_10
Patent number
US05254718

Reaction notes

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