Hydrochloric Acid → HCID 19024759, compound

HRID 1034065Notes

Reaction equation

HRID 1034065 reaction equation
[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>CN(C)C=O>[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:8][CH:7]=1)[C:3]([O:5][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 13647430HCID 13647430, compound

Product 1

HCID 19024759HCID 19024759, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxy-2-(4-isobutylphenyl)acetic acid (3.8 g) in N,N-dimethylformamide (30 ml) was added potassium carbonate (7.6 g) and benzylbromide (2.2 ml). The mixture was stirred at room temperature for 4.5 hours and poured into ice water and 7% hydrochloric acid. The organic layer was extracted with ethyl acetate, washed with aqueous sodium bircarbonate solution and water, dried over magnesium sulfate and evaporated. The residual white powder was collected with n-hexane by filtration to give benzyl 2-hydroxy-2-(4-isobutylphenyl)acetate as a white powder (4.42 g).

Workup

  1. extractionThe organic layer was extracted with ethyl acetate
  2. washwashed with aqueous sodium bircarbonate solution and water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. filtrationThe residual white powder was collected with n-hexane by filtration

Sources & evidence

ORD record
ord-8d5d493df27947c4a02728af91e36e44
Source dataset
uspto-grants-1994_05
Patent number
US05312829

Reaction notes

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