Benzoyl chloride → HCID 70620144, compound

HRID 1679559Notes

Reaction equation

HRID 1679559 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:12][C:11]2[C:6](=[C:7]([O:15][CH3:16])[CH:8]=[CH:9][C:10]=2[O:13][CH3:14])[CH2:5][C@H:4]1[OH:17].[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+]>O.C1C=CC=CC=1>[C:18]([NH:2][C@@H:3]1[CH2:12][C:11]2[C:6](=[C:7]([O:15][CH3:16])[CH:8]=[CH:9][C:10]=2[O:13][CH3:14])[CH2:5][C@H:4]1[OH:17])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 131710713HCID 131710713, compound

Product 1

HCID 70620144HCID 70620144, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent2×

Procedure

A solution of 74.8 g of trans-3-amino-1,2,3,4-tetrahydro-5,8-dimethoxy-2- naphthalenol, hydrochloride in 2 liters of water is cooled in an ice bath and a solution of 40 g of benzoyl chloride in 300 ml of benzene is added. While stirring vigorously a solution of 23 g of sodium hydroxide in 100 ml of water is added dropwise at 0°-5° C over a period of 30 minutes. Semi-solid material begins adhering to the sides of the flask almost immediately. The mixture is stirred at 0°-5° C for an additional 2 hours. The solid is removed by filtration, washed with a small amount of water, then washed with chloroform and dried in vacuo over phosphorous pentoxide to give 78.5 g of the title compound.

Workup

  1. additionis added dropwise at 0°-5° C over a period of 30 minutes
  2. customThe solid is removed by filtration
  3. washwashed with a small amount of water
  4. washwashed with chloroform
  5. dry with materialdried in vacuo over phosphorous pentoxide

Sources & evidence

ORD record
ord-971be30c7b814c69a6d16ef1ff89dd9a
Source dataset
uspto-grants-1978_03
Patent number
US04081444

Reaction notes

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