Methanol → 2-(Oxolan-2-yl)acetic acid

HRID 482998Notes

Reaction equation

HRID 482998 reaction equation
[C:1]([CH2:3][CH:4]1[CH2:8][CH2:7][CH2:6][O:5]1)#N.[OH-:9].[Na+].C[OH:12]>O>[O:5]1[CH2:6][CH2:7][CH2:8][CH:4]1[CH2:3][C:1]([OH:12])=[O:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4962721(Tetrahydrofuran-2-yl)acetonitrile

Product 1

HCID 2287262-(Oxolan-2-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 90 g. (0.81 mole) 2-cyanomethyltetrahydrofuran, 130 g. (3.2 mole) sodium hydroxide, 250 ml. methanol and 300 ml. water was heated at reflux for 20 hours. The reaction mixture was evaporated in vacuo, the residue taken up in chloroform and acidified to pH 5 with 6N hydrochloric acid. The organic layer was separated, the aqueous phase extracted with chloroform, the combined extracts dried (MgSO4) and the solvent evaporated to give 62 g. of crude acid. Distillation afforded 52.6 g. of product, B.P. 110° C. (2 mm.). 1H-NMR (CDCl3) ppm (delta): 2.50 (d, 2H, CH2COOH), 11.10 (s, 1H, COOH).

Workup

  1. temperatureat reflux for 20 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. customThe organic layer was separated
  4. extractionthe aqueous phase extracted with chloroform
  5. dry with materialthe combined extracts dried (MgSO4)
  6. customthe solvent evaporated
  7. customto give 62 g
  8. distillationDistillation
  9. customafforded 52.6 g

Sources & evidence

ORD record
ord-7b276b508afd4800aa1c9c4133ea707b
Source dataset
uspto-grants-1986_03
Patent number
US04576964

Reaction notes

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