Hydrochloric Acid → 2-[(Benzoyloxy)methyl]benzoic acid

HRID 485071Notes

Reaction equation

HRID 485071 reaction equation
[C:1]1([C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][O:3]1)=[O:2].[OH-:11].[Na+].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>O>[C:13]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[C:1]([OH:2])=[O:11])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6885PhthalideHCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 940032-[(Benzoyloxy)methyl]benzoic acidYield 38.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Phthalide (134 g, 1 mole) is dissolved in 20% NaOH (715 ml, 3.58 mole) by heating the mixture to about 60° C. The obtained solution is diluted with water (750 ml) and ice (5 kg). Benzoyl chloride (151 ml, 1.3 mole) is added in 10 minutes with vigorous stirring and about 1 hour later the pH of the reaction mixture is brought to 2.5 by the addition of 10% HCl (750 ml). The solid which is collected under vacuum filtration is washed carefully with warm water (4×1500 ml) and crystallized from ethanol/water 7/3 (800 ml), yielding 98.2 g of 2-benzoyloxymethylbenzoic acid. M.p. 118°-124° C.

Workup

  1. filtrationThe solid which is collected under vacuum filtration
  2. washis washed carefully with warm water (4×1500 ml)
  3. customcrystallized from ethanol/water 7/3 (800 ml)

Sources & evidence

ORD record
ord-472190f20b5e41a7846178544c731ad4
Source dataset
uspto-grants-1985_08
Patent number
US04535090

Reaction notes

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