Benzyl Alcohol → 1,5-Pentanedioic Acid Monobenzyl Ester

HRID 992587Notes

Reaction equation

HRID 992587 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH2:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C=CC=CC=1>[CH2:9]([O:16][C:5]([CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8])=[O:6])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 7940Glutaric anhydride

Product 1

HCID 110532341,5-Pentanedioic Acid Monobenzyl Ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of glutaric anhydride (11.4 g, 0.1 mol) and benzyl alcohol (11.4 mL, 1.1 equiv.) in toluene (200 mL) was heated at 70° C. for 2 days. Solvent was evaporated at reduced pressure to give the product which was dried under high vacuum and was pure enough to use in the next step. 1H NMR (CDCl3): δ1.96 (t, J=7.2 Hz, 2H), 2.44 (q, J=7.0 Hz, 4H), 5.13 (s, 2H), 7.33 (s, 5H).

Workup

  1. customSolvent was evaporated at reduced pressure
  2. customto give the product which
  3. customwas dried under high vacuum

Sources & evidence

ORD record
ord-4e290f5e087f42ef88f7fe678145204a
Source dataset
uspto-grants-2002_10
Patent number
US06469065B1

Reaction notes

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