Benzoyl chloride → HCID 13531099, compound

HRID 464490Notes

Reaction equation

HRID 464490 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 100ml. 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-4675c0be0fd942f99df8c3bf3c5b0bff
Source dataset
uspto-grants-1985_10
Patent number
US04547584

Reaction notes

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