Water → HCID 86614071, compound

HRID 2243174Notes

Reaction equation

HRID 2243174 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:15][O:14][CH:13]([O:16][CH3:17])[CH2:12][O:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 69184Benzaldehyde, 2-hydroxy-5-methyl-HCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 86614071HCID 86614071, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg (0.73 mmol) of 2-hydroxy-5-methyl-benzaldehyde in DMF (1 ml) were added 109 μl (0.92 mmol) of 2-bromo-1,1-dimethoxy-ethane and 112 mg (0.81 mmol) of potassium carbonate. The reaction mixture was heated to reflux for 90 min. Then water was added at RT and the mixture was extracted with ether. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to yield 2-(2,2-dimethoxy-ethoxy)-5-methyl-benzaldehyde as a yellow oil (154 mg, 93%). 1HNMR (CDCl3, 300 MHz): δ 2.32 (s, 3H), 3.48 (s, 6H), 4.09 (d, J=5.3 Hz, 2H), 4.75 (t, J=5.3 Hz, 1H), 6.89 (d, J=8.4 Hz, 1H), 7.34 (dd, J=8.4 and 2.3 Hz, 1H), 7.64 (d, J=2.3 Hz, 1H), 10.48 (s, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 90 min
  3. extractionthe mixture was extracted with ether
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8f075a29109649ea94e4e63cfce72d4c
Source dataset
uspto-grants-2010_03
Patent number
US07674815B2

Reaction notes

Loading…