Benzoyl chloride → HCID 13531099, compound

HRID 1380017Notes

Reaction equation

HRID 1380017 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([OH:18])[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19](OC1C=C(O)C=CC=1OC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C.C(Cl)(=O)C1C=CC=CC=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:11]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 135310983-(Benzyloxy)-4-methoxyphenolHCID 13531100HCID 13531100, compound

Product 1

HCID 13531099HCID 13531099, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The compound 3-hydroxy-4-methoxyphenyl benzoate was made as follows. An amount of 2.00 gms. of 3-benzyloxy-4-methoxyphenol, 1.00 gms. of triethylamine and 0.10 gms of 4-dimethylaminopyridine were dissolved in 100 ml. of methylene chloride at 0° C. and stirred. To the mixture was added 1.22 gms. of benzoyl chloride and the mixture was stirred overnight. The mixture was then washed with equal volumes of 1M hydrochloric acid, saturated sodium bicarbonate and water. The mixture was then dried over magnesium sulfate and the solvent evaporated to yield 3-benzyloxy-4-methoxyphenyl benzoate.

Workup

  1. additionTo the mixture was added 1.22 gms
  2. washThe mixture was then washed with equal volumes of 1M hydrochloric acid, saturated sodium bicarbonate and water
  3. dry with materialThe mixture was then dried over magnesium sulfate
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-d3f2c17b43d948ae9a4552467f9aae54
Source dataset
uspto-grants-1986_04
Patent number
US04579748

Reaction notes

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