4-Methoxybenzyl alcohol → p-Methoxybenzyl 4-carboxy-4-methylvalerate

HRID 1252216Notes

Reaction equation

HRID 1252216 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:8][CH2:7][C:6](=[O:9])[O:5][C:3]1=[O:4].[OH:11][CH2:12][C:13]1[CH:20]=[CH:19][C:16]([O:17][CH3:18])=[CH:15][CH:14]=1.C(N(CC)CC)C>O1CCOCC1>[C:3]([C:2]([CH3:10])([CH3:1])[CH2:8][CH2:7][C:6]([O:11][CH2:12][C:13]1[CH:20]=[CH:19][C:16]([O:17][CH3:18])=[CH:15][CH:14]=1)=[O:9])([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 8471TriethylamineHCID 76247Dihydro-3,3-dimethyl-2H-pyran-2,6(3H)-dione

Product 1

HCID 20140782p-Methoxybenzyl 4-carboxy-4-methylvalerate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,2-dimethylglutaric anhydride (19.34 g), anise alcohol (22.08 g) and triethylamine (19.39 g) in dry dioxane (360 ml) was stirred at 80° C. for 3.5 hours. The reaction mixture was evaporated and the residue was diluted with water and adjusted to pH 9 with potassium carbonate. The aqueous layer was washed with benzene, acidified with dilute hydrochloric acid and extracted with benzene. The extract was washed with water, dried over anhydrous sodium sulfate and evaporated to give p-methoxybenzyl 4-carboxy-4-methylvalerate.

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe residue was diluted with water
  3. washThe aqueous layer was washed with benzene
  4. extractionextracted with benzene
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-b098b3b1ed444003b5fa770d4f851bf6
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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