Hydrochloric Acid → HCID 19603686, compound

HRID 1604644Notes

Reaction equation

HRID 1604644 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH:11]([CH2:28][CH2:29][CH3:30])[C:12]([O:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.O>[CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[O:1][CH:11]([CH2:28][CH2:29][CH3:30])[C:12]([O:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 19603754HCID 19603754, compound

Product 1

HCID 19603686HCID 19603686, compoundYield 103.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 2-hydroxybenzaldehyde (2.44 g), diphenylmethyl 2-bromopentanoate (7.26 g), and potassium carbonate (3.45 g) in dimethylsulfoxide (20 ml) was stirred at room temperature for 5 hours. The mixture was diluted with water, neutralized with 1N hydrochloric acid, and was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate, and concentrated to give diphenylmethyl 2-(2-formylphenoxy)-pentanoate (8.04 g).

Workup

  1. extractionwas extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dcc4b9704b724f2b910a0b3779b52f08
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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