Water → 1,2-Dibenzyloxy-2-hydroxy-3,4-dichlorobenzene

HRID 1982264

Reaction equation

HRID 1982264 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[C:4]([OH:9])[C:3]=1[OH:10].[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH2:21]>CN(C)C=O>[CH2:13]([O:9][CH:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[C:3]1([O:21][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[OH:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 198773,4-DichlorocatecholHCID 24758Sodium hydride

Product 1

HCID 233177331,2-Dibenzyloxy-2-hydroxy-3,4-dichlorobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 250 ml of dimethylformamide is dissolved 8.95 g of the compound (II), and 4.80 g (2 equivalent) of 50% sodium hydride oily suspension and 10.25 g (1.3 equivalent) of benzyl bromide are added thereto. The mixture is stirred for 10 minutes under ice cooling, then poured into 200 ml of water, and sparingly soluble crystals are collected by filtration and recrystallized from hexane to give 2.096 g of 1,2-dibenzyloxy-2-hydroxy-3,4-dichlorobenzene, mp. 74°-75° C.

Workup

  1. additionare added
  2. filtrationare collected by filtration
  3. customrecrystallized from hexane

Sources & evidence

ORD record
ord-8e725f34052144fb81d94d40b125487e
Source dataset
uspto-grants-1986_06
Patent number
US04595767

Linked notes

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