Benzyl Chloride → HCID 12851607, compound

HRID 2296053Notes

Reaction equation

HRID 2296053 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][C:9]=1[OH:10].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([O:10][C:9]1[C:8]([CH3:7])=[C:14]([OH:15])[CH:13]=[CH:12][CH:11]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 118432-Methylresorcinol

Product 1

HCID 12851607HCID 12851607, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

Anhydrous potassium carbonate (30.4 g) was added to a stirred solution of 2-methylresorcinol (24.8 g) in N,N-dimethylformamide (DMF, 250 ml) and benzyl chloride (25.3 g) was added over 15 minutes. The mixture was heated to 80° C. and maintained at this temperature overnight with continued stirring. On cooling the DMF was removed in vacuo to give an oil which was partitioned between water and ether. The dried ethereal phase was evaporated and chromatographed on silica eluting with chloroform to give 9.78 g (23%) of the title compound of mp 58°-59° C. (Found: C, 78.16; H, 6.63; C14H14O2 requires C, 78.48; H, 6.58%).

Workup

  1. additionwas added over 15 minutes
  2. temperaturemaintained at this temperature overnight with continued stirring
  3. customwas removed in vacuo
  4. customto give an oil which
  5. customwas partitioned between water and ether
  6. customThe dried ethereal phase was evaporated
  7. customchromatographed on silica eluting with chloroform

Sources & evidence

ORD record
ord-111a29d790134895bfdd5b8be9061865
Source dataset
uspto-grants-1984_01
Patent number
US04427686

Reaction notes

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