Water → HCID 57801021, compound

HRID 2101239Notes

Reaction equation

HRID 2101239 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([C:7](=[O:13])[CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])=[CH:3][CH:2]=1.O>C(OCC)C>[C:1]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:2]=[CH:3][C:4]([CH:7]([OH:13])[CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 962WaterHCID 57801035HCID 57801035, compound

Product 1

HCID 57801021HCID 57801021, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Biphenyl-4-yl-hex-5-en-1-one (1 g) was dissolved in diethyl ether (25 ml) NaBH4 (2.5 g) was added and the mixture stirred for 30 minutes. Water (50 ml) was added and most of the solvent evaporated under vacuo. The residue was poured into water and the product extracted with ethyl acetate. The organic layer was dried (Na2SO4) and the ethyl acetate evaporated under vacuum to give a white solid. δC (CDCl3, 62.9 MHz): 25.2, 33.6, 38.5, 74.3, 114.8, 126.4, 127.1, 127.2, 128.8, 138.6, 140.5, 140.9 and 143.9.

Workup

  1. additionwas added
  2. customevaporated under vacuo
  3. additionThe residue was poured into water
  4. extractionthe product extracted with ethyl acetate
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customthe ethyl acetate evaporated under vacuum
  7. customto give a white solid

Sources & evidence

ORD record
ord-db7ccc441e0b48379d7fe977f0d37345
Source dataset
uspto-grants-2009_08
Patent number
US07572825B2

Reaction notes

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