Hydrochloric Acid → 4-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]phenylmethanol

HRID 2268496Notes

Reaction equation

HRID 2268496 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:14]2[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][O:22][C:23]3[CH:33]=[CH:32][C:26]([C:27](OCC)=[O:28])=[CH:25][CH:24]=3)[CH2:18][CH2:19][C:13]=2[C:12]([O:34][CH3:35])=[C:11]([O:36][CH3:37])[C:10]=1[O:38][CH3:39].Cl>C(OCC)C.C1COCC1.O>[CH3:35][O:34][C:12]1[C:13]2[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][O:22][C:23]3[CH:24]=[CH:25][C:26]([CH2:27][OH:28])=[CH:32][CH:33]=3)[CH2:16][CH2:15][C:14]=2[C:9]([O:8][CH3:7])=[C:10]([O:38][CH3:39])[C:11]=1[O:36][CH3:37]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 18348644Ethyl 4-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 183485334-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]phenylmethanolYield 63.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (91.8 mg) in diethyl ether (10 ml) was dropwise added a solution of ethyl 4-[2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoate (553 mg) in THF (10 ml) with cooling with ice. After stirring was continued for 15 min, 10% hydrochloric acid was added to the reaction mixture, which was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was recrystallized from hexane-ethyl acetate to yield the entitled compound (320 mg) as crystals.

Workup

  1. temperaturewith cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-a9ebfb5512ee46e08197e211a5c16d90
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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