Hydrochloric Acid → HCID 86590126, compound

HRID 1884918Notes

Reaction equation

HRID 1884918 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([OH:30])=[C:12]([C:28]=1[CH3:29])[C:13]([C:15]1[C:20]([CH3:21])=[CH:19][C:18]([O:22][CH3:23])=[C:17]([O:24][CH3:25])[C:16]=1[O:26][CH3:27])=[O:14].Cl>O1CCCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([OH:30])=[C:12]([C:28]=1[CH3:29])[CH:13]([OH:14])[C:15]1[C:20]([CH3:21])=[CH:19][C:18]([O:22][CH3:23])=[C:17]([O:24][CH3:25])[C:16]=1[O:26][CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 22671391HCID 22671391, compound

Product 1

HCID 86590126HCID 86590126, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At −20° C., under an atmosphere of protective gas, 3 mmol of a 1-molar solution of LiAlH4 in tetrahydrofuran (THF) were added dropwise to a solution of 0.86 g of 5-chloro-2-hydroxy-6,6′-dimethyl-2′, 3′, 4′-trimethoxybenzophenone in 10 ml of anhydrous THF. The reaction mixture was warmed to room temperature and then admixed with ice water, acidified with dilute hydrochloric acid and extracted with ethyl acetate. The combined organic phases were washed with sat. NaCl solution, dried and purified by column chromatography (mobile phase: ethyl acetate/cyclohexane 3:7). This gave 0.46 mg of the title compound as a white solid of m.p. 140-142° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed with sat. NaCl solution
  3. customdried
  4. custompurified by column chromatography (mobile phase: ethyl acetate/cyclohexane 3:7)

Sources & evidence

ORD record
ord-9f08fd0f06994c039fc350a342f3ba72
Source dataset
uspto-grants-2004_07
Patent number
US06767923B2

Reaction notes

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