5,7-dimethyl-8-methoxy-9-(2,2-diethoxyethyl)-1,2,3,4-tetrahydro-9H-fluorene → 5,7-dimethyl-8-methoxy-9-formylmethyl-1,2,3,4-tetrahydro-9H-fluorene

HRID 2051420Notes

Reaction equation

HRID 2051420 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([CH3:15])[C:12]([O:16][CH3:17])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=1[CH:10]2[CH2:18][CH:19](OCC)[O:20]CC>O1CCCC1.Cl>[CH3:1][C:2]1[CH:14]=[C:13]([CH3:15])[C:12]([O:16][CH3:17])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=1[CH:10]2[CH2:18][CH:19]=[O:20]

Participants

4

Reactant 1

HCID 151572005,7-dimethyl-8-methoxy-9-(2,2-diethoxyethyl)-1,2,3,4-tetrahydro-9H-fluorene

Product 1

HCID 151572015,7-dimethyl-8-methoxy-9-formylmethyl-1,2,3,4-tetrahydro-9H-fluoreneYield 105.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran solution containing 1.45 g of 5,7-dimethyl-8-methoxy-9-(2,2-diethoxyethyl)-1,2,3,4-tetrahydro-9H-fluorene in 10 ml of tetrahydrofuran and 10 ml of 15% hydrochloric acid were stirred at room temperature for 3 hours. The reaction mixture was extracted with dichloromethane and the extract was washed with saturated aqueous sodium chloride solution and saturated sodium bicarbonate solution and then dried with magnesium sulfate. The solvent was distilled off to obtain 1.20 g of 5,7-dimethyl-8-methoxy-9-formylmethyl-1,2,3,4-tetrahydro-9H-fluorene.

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane
  2. washthe extract was washed with saturated aqueous sodium chloride solution and saturated sodium bicarbonate solution
  3. dry with materialdried with magnesium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-640fd08a464d4fdab2c0473be67990b7
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

Loading…