Benzyl Chloride → HCID 21544507, compound

HRID 1606755Notes

Reaction equation

HRID 1606755 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[H-].[Na+].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH2:15]([O:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([O:6][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1)=[O:5])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 757875-Methoxysalicylic Acid

Product 1

HCID 21544507HCID 21544507, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5.0 g. (0.03 mole) of 2-hydroxy-5-methoxybenzoic acid in 50 ml. of dimethylformamide is treated with 2.5 g. (0.06 mole) of sodium hydride in a 56.6% oil suspension, followed by the addition of 7.6 g. (0.06 mole) of benzyl chloride. The resulting mixture is heated at 98°-103° C. for one hour, after which the insolubles are filtered, the filtrate diluted with 100 ml. of water and the aqueous solution extracted with ether. The aqueous phase is discarded and the ether phase dried over sodium sulfate and evaporated to provide the intermediate, benzyl 2-benzyloxy-5-methoxybenzoate, as an oil, 5.0 g.

Workup

  1. temperatureThe resulting mixture is heated at 98°-103° C. for one hour
  2. filtrationafter which the insolubles are filtered
  3. additionthe filtrate diluted with 100 ml
  4. extractionof water and the aqueous solution extracted with ether
  5. dry with materialthe ether phase dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-d8b8f97a676b498d9ffe32da69865f6c
Source dataset
uspto-grants-1976_04
Patent number
US03953595

Reaction notes

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