Acrolein → HCID 20163034, compound

HRID 246843Notes

Reaction equation

HRID 246843 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([OH:10])=[O:9].C([Li])CCC.[CH:17]([CH:19]=[CH2:20])=[O:18]>C1COCC1>[OH:18][CH:17]([CH:19]=[CH2:20])[CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:11])[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 7847AcroleinHCID 69519o-Tolylacetic acidHCID 178418339Butyllithium

Product 1

HCID 20163034HCID 20163034, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of o-tolylacetic acid (45.0 g.) in dry THF (300 ml.) was treated under argon at 5°-10° C. with a 1.60M solution (376 ml.) of butyl lithium. The suspension was stirred 2 hours at 5°-10° C. and then acrolein (dried over 3A molecular sieve) (20.0 ml., 16.8 g.) was added over 5 minutes. The mixture was stirred for 2 hours and then carefully treated with ice-water (1 1.) The aqueous mixture was washed with ether (200 ml.). The aqueous layer was separated and acidified to pH4 (HCl) and extracted with ether (3×150 ml.). The extracts were washed with water, dried (magnesium sulphate) and evaporated to give 3-hydroxy-2-o-tolyl-4-pentenoic acid (A) (55.2 g.), which was used without purification.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. washwas washed with ether (200 ml.)
  3. customThe aqueous layer was separated
  4. extractionextracted with ether (3×150 ml.)
  5. washThe extracts were washed with water
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated

Sources & evidence

ORD record
ord-05a0c4086a1345eba95df6b76559a3d9
Source dataset
uspto-grants-1987_11
Patent number
US04704399

Reaction notes

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