Acetic Acid → HCID 68601732, compound

HRID 1951969Notes

Reaction equation

HRID 1951969 reaction equation
[BH4-].[Li+].C(O[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:10][CH:9]=1)(=O)C.[Cl-].[NH4+].[C:23](O)(=[O:25])C>O1CCCC1>[CH3:20][O:19][CH2:18][CH2:17][O:16][CH2:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][CH2:23][OH:25])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 68600595HCID 68600595, compound

Product 1

HCID 68601732HCID 68601732, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

2.7 g (122.3 mmol) of lithium borohydride is added to a solution of 10 g (41 mmol) of [4-(2-methoxy-ethoxymethoxy)-phenyl]-methyl acetate in 100 ml of tetrahydrofuran. The reaction mixture is stirred at 60° C. for 4 h. After cooling, the reaction mixture is poured into a mixture of ice and saturated aqueous ammonium chloride solution, acidified with aqueous solution of acetic acid of concentration 1M and then extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution, and dried over magnesium sulfate. After evaporation of the solvents, 8.9 g (97%) of 2-[4-(2-methoxy-ethoxymethoxy)-phenyl]-ethanol is obtained in the form of a colorless oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvents

Sources & evidence

ORD record
ord-4a88c288f4b741cdae7bfa21f606f7d9
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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