Water → (1,1'-Biphenyl)-4-methanol

HRID 1657691Notes

Reaction equation

HRID 1657691 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH:18]([OH:21])(C)C.O.C[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>>[C:11]1([C:17]2[CH:24]=[CH:25][C:26]([CH2:18][OH:21])=[CH:27][CH:28]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 3776IsopropanolHCID 8058HexaneHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19186(1,1'-Biphenyl)-4-methanol

Procedure

At -60° C., 20 ml. of a 20% solution of diisobutyl-aluminum hydride in hexane was added to a solution of 2 g. of 2-[3α-p-biphenyl-carbonyloxy-5α-hydroxy-2β-(3,3-ethylenedioxy-octan-1-yl)-cyclopent-1α-yl]-acetic acid γ-lactone in 60 ml. of toluene. After 20 minutes, 3 ml. of isopropyl alcohol was added dropwise to the reaction mixture, the latter was heated to room temperature, mixed with 10 ml. of water, and agitated for 10 minutes. The mixture was thereafter extracted with ethyl acetate and the ethyl acetate solution was shaken with NaCl solution, dried over magnesium sulfate, and evaporated to dryness under vacuum. The residue was filtered with ether over 45 g. of silica gel, the elution yielding first p-phenylbenzyl alcohol. With ether/dioxane (9 + 1), 1.05 g. of 2-[3α,5α-dihydroxy-2β-(3,3-ethylenedioxy-octan-1-yl)-cyclopent-1α-yl]-acetaldehyde γ-hemiacetal was obtained as a colorless oil. The thin-layer chromatogram (ether/dioxane 2 + 1) showed a uniform spot having an Rf value of 0.23.

Workup

  1. customAt -60° C.
  2. additionmixed with 10 ml
  3. extractionThe mixture was thereafter extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness under vacuum
  6. filtrationThe residue was filtered with ether over 45 g
  7. washof silica gel, the elution

Sources & evidence

ORD record
ord-2913ca4672b54d529b61975affd24882
Source dataset
uspto-grants-1976_06
Patent number
US03962218

Reaction notes

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