Hydrochloric Acid → 4-(2-Carboxyethoxy)-2-methylbenzaldehyde

HRID 1442416Notes

Reaction equation

HRID 1442416 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([CH3:10])[CH:3]=1.CC(C)([O-])C.[K+].[C:17]1(=[O:21])[O:20][CH2:19][CH2:18]1.Cl>O1CCCC1>[C:17]([CH2:18][CH2:19][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([CH3:10])[CH:3]=1)([OH:21])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2365Beta-PropiolactoneHCID 4581854-Hydroxy-2-methylbenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 230778584-(2-Carboxyethoxy)-2-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-hydroxy-2-methylbenzaldehyde (5 g) and potassium tert-butoxide (4.12 g) in tetrahydrofuran (60 mL) was added β-propiolactone (4.6 mL), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was suspended in ethyl acetate (20 mL)-n-hexane (100 mL). The insoluble material was collected by filtration, and washed with n-hexane and dried under reduced pressure to give the title compound (7.2 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. filtrationThe insoluble material was collected by filtration
  6. washwashed with n-hexane
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-6cef30415ab74e44be9409039115f951
Source dataset
uspto-grants-2010_02
Patent number
US07655632B2

Reaction notes

Loading…