Water → 4-[2-Benzyloxybenzylthio]benzoic acid

HRID 1006022Notes

Reaction equation

HRID 1006022 reaction equation
[H-].[Na+].[CH:3]1[C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=[C:5]([SH:12])[CH:4]=1.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27]Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C=O)C.C(O)(=O)C>[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][S:12][C:5]1[CH:6]=[CH:7][C:8]([C:9]([OH:11])=[O:10])=[CH:3][CH:4]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 957384-Mercaptobenzoic acidHCID 15142522-Benzyloxybenzylbromide

Product 1

HCID 226755514-[2-Benzyloxybenzylthio]benzoic acidYield 105.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (6.5 g, 50% dispersion in oil) in DMF (100 ml) was cooled (0° C., ice bath) and 4-thiobenzoic acid (10 g) was added. After stirring for 30 minutes at 0° C., 2-bromomethylphenyl benzyl ether (18.6 g) as a solution in DMF (100 ml) was added. The reaction was stirred at ambient temperature for 18 hours, cooled (ice bath), water was added, and the mixture acidified with acetic acid. The resulting solid was isolated by filtration and recrystallised from methanol to give 4-[2-benzyloxybenzylthio]benzoic acid (24 g) (mpt. 144° C.).

Workup

  1. additionwas added
  2. stirringThe reaction was stirred at ambient temperature for 18 hours
  3. additionwas added
  4. customThe resulting solid was isolated by filtration
  5. customrecrystallised from methanol

Sources & evidence

ORD record
ord-ffbd9f163f7f4392b863fca63fae43b7
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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