Hydrochloric Acid → HCID 43509986, compound

HRID 2241887Notes

Reaction equation

HRID 2241887 reaction equation
[Na].C([O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[C:16]2[O:17][C:18]([CH3:21])([CH3:20])[CH2:19][C:15]=2[CH:14]=[CH:13][CH:12]=1)(=O)C.O.Cl>CO>[CH3:20][C:18]1([CH3:21])[O:17][C:16]2[C:11]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][OH:5])=[CH:12][CH:13]=[CH:14][C:15]=2[CH2:19]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5360545SodiumHCID 59204835HCID 59204835, compound

Product 1

HCID 43509986HCID 43509986, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

With stirring, a solution of 2.24 grams (0.056 mole) of sodium ydroxide in 125 mL of methanol was added 8.0 grams (0.028 mole) of 4-(2,2-dimethyl-2,3-dihydrobenzo[2,3-b]furan-7-yloxy)butyl acetate. Upon completion of addition the reaction mixture was stirred at ambient temperature during a three-hour period. After this time 150 mL of water was added to the reaction mixture, and the mixture was acidified to a pH of 6 with concentrated hydrochloric acid. The mixture was then extracted with four 50 mL portions of diethyl ether. The combined extracts were washed with one 50 mL portion of water, dried with sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure, yielding 5.6 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. stirringwas stirred at ambient temperature during a three-hour period
  3. extractionThe mixture was then extracted with four 50 mL portions of diethyl ether
  4. washThe combined extracts were washed with one 50 mL portion of water
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6bdc0a08e8094bdea7b86e4a07cdaa0f
Source dataset
uspto-grants-2010_03
Patent number
US07671055B2

Reaction notes

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