Toluene → (4-Methyloxan-4-yl)acetic acid

HRID 387201Notes

Reaction equation

HRID 387201 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[C:8]([CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:10]CC)=[O:9].[C:33]1(C)C=CC=CC=1>>[CH3:33][C:4]1([CH2:13][C:8]([OH:10])=[O:9])[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 121599Tetrahydro-4H-pyran-4-one

Product 1

HCID 58678636(4-Methyloxan-4-yl)acetic acid

Conditions

Temperature
110 °C

Procedure

To a solution of dihydro-2H-pyran-4(3H)-one (X9) (3.13 g, from Aldrich) in toluene was added (carbethoxymethylene)-triphenylphosphorane (12.0 g, Aldrich). The solution was stirred at 110° C. for 3 days. The resulting dark solution was concentrated in vacuo and the residue directly purified by column over silica gel to yield compound X10 (4.54 g) as a clear liquid. 1H-NMR (CDCl3, 500 MHz): 5.66 (s, 1H), 4.16 (q, 2H), 3.98 (s, 4H), 3.00 (t, 2H), 2.38 (m, 2H), 1.77 (m, 4H), 1.27 (t, 3H) ppm.

Workup

  1. concentrationThe resulting dark solution was concentrated in vacuo
  2. customthe residue directly purified by column over silica gel
  3. customto yield compound X10 (4.54 g) as a clear liquid

Sources & evidence

ORD record
ord-10f6dda28b5b413d81a0ecc4bab12040
Source dataset
uspto-grants-2013_02
Patent number
US08372873B2

Reaction notes

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