(2-Hydroxyphenyl)acetic acid → HCID 22035799, compound

HRID 1790789Notes

Reaction equation

HRID 1790789 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].CC(C)([O-])C.[K+].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>CN(C)C=O>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH2:24][C:23]1[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1)=[O:10]

Participants

5

Reactant 3

HCID 11970(2-Hydroxyphenyl)acetic acidHCID 699934-Methyloxybenzyl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 22035799HCID 22035799, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-hydroxyphenylacetic acid (10 g, 66 mmol) was dissolved in N,N-dimethylformamide (100 ml) and cooled on ice-bath. Potassium tert-butoxide (8.85 g, 78 mmol) was added. The mixture was left for 30 min and allowed to reach room temperature. 4-Methoxy-benzylchloride (11.7 g, 72 mmol) in N,N-dimethylformamide (30 ml) was then added dropwise, under nitrogen atmosphere and left over-night. The solvent was evaporated under reduced pressure and the crude mixture was dissolved in ether (100 ml) and washed with water (25 ml), brine and dried over sodium sulphate. Chromatography (hexane-ethyl acetate, 2:1) followed by recrystallization (hexane-ethyl acetate) gave the title compound (7.6 g, 42%).

Workup

  1. temperaturecooled on ice-bath
  2. customto reach room temperature
  3. waitleft over-night
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionthe crude mixture was dissolved in ether (100 ml)
  6. washwashed with water (25 ml), brine
  7. dry with materialdried over sodium sulphate
  8. customChromatography (hexane-ethyl acetate, 2:1) followed by recrystallization (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-7b3a7ee360b1461e8cd3f42ab200f8fa
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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