Acetic Acid → 4-(4-(4-Chlorophenyl)-1-hydroxybutyl)phenol

HRID 2253756Notes

Reaction equation

HRID 2253756 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]([OH:42])[CH2:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)=[CH:27][CH:26]=1)(C)C.CC(O)=O>C1COCC1>[Cl:41][C:38]1[CH:39]=[CH:40][C:35]([CH2:34][CH2:33][CH2:32][CH:31]([C:28]2[CH:27]=[CH:26][C:25]([OH:24])=[CH:30][CH:29]=2)[OH:42])=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 538578064-(4-Chlorophenyl)-1-(4-t-butyldiphenylsiloxy phenyl)butanol

Product 1

HCID 197458724-(4-(4-Chlorophenyl)-1-hydroxybutyl)phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., 1M tetrabutylammonium fluoride (100 mL) was added to a solution of the silyl ether of Step 2 (34 g) and AcOH (15 mL) in THF (200 mL) and the reaction mixture was stirred at 0° C. 2.5 hours. 25% aqueous NH4OAc was then added and the product was extracted with EtOAc, dried over MgSO4 and purified by a swish in EtOAc:hexane 1:2. The title compound so obtained was used as such for the next step.

Workup

  1. custom2.5 hours
  2. extractionthe product was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. custompurified by a swish in EtOAc:hexane 1:2

Sources & evidence

ORD record
ord-fd7a1b5326a241b2b75c562504967ad6
Source dataset
uspto-grants-1993_08
Patent number
US05232916

Reaction notes

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