Water → HCID 19812660, compound

HRID 466943Notes

Reaction equation

HRID 466943 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[O:21][CH3:22])[CH2:13][CH2:12]1.BrB(CC)CC.O>ClCCl>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[O:21][CH3:22])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 12475635HCID 12475635, compoundHCID 19812678HCID 19812678, compound

Product 1

HCID 19812660HCID 19812660, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution prepared from 490 mg (1.64 mmol) of 1-(2-methoxymethoxyphenyl)-1-(2-methoxy-4-methylphenyl)cyclopropane and 6.1 ml of a 1M solution (8.2 mmol) of bromodiethylborane in dichloromethane was stirred overnight under an argon atmosphere. Ten ml of water were added, the phases were separated, and the aqueous phase was extracted twice with 20 ml of dichloromethane. The combined organic extracts were dried over magnesium sulfate and concentrated by evaporation under reduced pressure to obtain 1-(2-hydroxyphenyl)-1-(2-methoxy-4-methylphenyl)cyclopropane. The proton NMR spectrum was consistent with the assigned structure. This was dissolved in 0.8 ml (8.2 mmol) of a 5M solution of bromodimethylborane and allowed to stir overnight. Nothing happened. The mixture was cooled to 0° C. and 3.3 ml (3.3 mmol) of a 1M solution of boron tribromide was added with stirring under an argon atmosphere. After a short reaction period 2 ml of water was added and the mixture was extracted with 2 ml of 5 percent aqueous sodium bicarbonate then with 2 ml of water, dried over magnesium sulfate and concentrated by evaporation under reduced pressure to obtain 350 mg (84 percent of theory) of the title compound as a foamy brown oil. The proton and carbon NMR spectra were consistent with the assigned structure.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted twice with 20 ml of dichloromethane
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-45dc009cec7449e8afbc9f46a4f110bc
Source dataset
uspto-grants-1992_10
Patent number
US05158597

Reaction notes

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