Potassium Carbonate → HCID 18947334, compound

HRID 1769164Notes

Reaction equation

HRID 1769164 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[C:4]([C:3]1[CH:8]=[C:9]([O:12][CH2:17][C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([Cl:13])[CH:15]=2)[CH:10]=[CH:11][C:2]=1[OH:1])([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 75077Methyl Gentisate

Product 1

HCID 18947334HCID 18947334, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Eight grams (47.62 mmoles) of the above ester was treated with 6.3 ml (47.62 mmoles) of 3-chlorobenzyl bromide and 8 grams potassium carbonate in 70 ml acetonitrile under reflux for 4 hours. The mixture was diluted with 100 ml ethyl acetate, filtered, and stripped in vacuo. The residue was recrystallized from ethanol to give 9.5 g of 2-Carbomethoxy-4-(m-chlorophenylmethyloxy)-phenol (62% yield from 2,5-dihydroxybenzoic acid).

Workup

  1. temperatureunder reflux for 4 hours
  2. filtrationfiltered
  3. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-86e6e89343e044cc87262f865631c13c
Source dataset
uspto-grants-1995_01
Patent number
US05380755

Reaction notes

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