Benzyl 4-Hydroxybenzoate → 4-[(Benzyloxy)carbonyl]phenyl 4-(acetyloxy)benzoate

HRID 1589675Notes

Reaction equation

HRID 1589675 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:25]([O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)(=[O:27])[CH3:26]>C1(C)C=CC=CC=1>[C:25]([O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([O:1][C:2]2[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:7])=[CH:4][CH:3]=2)=[O:34])=[CH:31][CH:30]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 8471TriethylamineHCID 2756254p-Acetoxybenzoyl chloride

Product 1

HCID 135877394-[(Benzyloxy)carbonyl]phenyl 4-(acetyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
30 °C

Procedure

A 200 ml. four-necked flask equipped with a condenser tube and a thermometer was charged with 36 g of p-acetoxybenzoic acid and 71.4 g of thionyl chloride, and they were reacted at 50° C. for 4 hours. The excess of thionyl chloride was evaporated under reduced pressure to give p-acetoxybenzoyl chloride. Then, a 300 ml four-necked flask equipped with a condenser tube, a thermometer and a dropping funnel was charged with 45.7 g of benzyl p-hydroxybenzoate, 20.2 g of triethylamine and 100 ml of toluene. The temperature of the flask was raised to 30° C., and a solution of 39.7 g of p-acetoxybenzoyl chloride in 50 g of toluene was added dropwise over 1 hour, and the reaction was carried out at 50° C. for 30 minutes. After cooling, the reaction mixture was washed with three 50 ml portions of water, and the solvent was evaporated under reduced pressure. Recrystallization of the residue from methanol gave benzyl p-(p-acetoxybenzoyloxy)benzoate.

Workup

  1. customThen, a 300 ml four-necked flask equipped with a condenser tube
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with three 50 ml portions of water
  4. customthe solvent was evaporated under reduced pressure
  5. customRecrystallization of the residue from methanol

Sources & evidence

ORD record
ord-87883dc8031241fd8e3e272d9e36c9c4
Source dataset
uspto-grants-1986_02
Patent number
US04573062

Reaction notes

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