Acetaldehyde → HCID 23346469, compound

HRID 1856274Notes

Reaction equation

HRID 1856274 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]2([CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:3]=1.C([Li])CCC.[CH:20](=[O:22])[CH3:21].O>O1CCCC1.CCCCCC>[C:4]12([CH2:14][CH2:13][CH2:12][CH2:11]1)[C:5]1[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:2]([CH:20]([OH:22])[CH3:21])=[CH:3]2

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 962WaterHCID 23346455HCID 23346455, compoundHCID 178418339Butyllithium

Product 1

HCID 23346469HCID 23346469, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

3'-Bromospiro(cyclopentane-1,1'-indene) (23 g) is dissolved in tetrahydrofuran (200 ml) and cooled to -70° C. While stirring under nitrogen, n-butyllithium (75 ml of a 2 M solution in hexane) is added followed after 30 minutes by acetaldehyde (14 g) in one portion. Stirring and cooling is maintained for 30 minutes whereupon the mixture is allowed to come to about 20° C. and is kept there for 2 hours. Water (600 ml) is then added and the solution is extracted three times with diethyl ether. The ether extracts are washed, dried over sodium sulphate and the ether is distilled off. Distillation of the residual oil gives the title alcohol, b.p. 139° C./0.4 torr.

Workup

  1. stirringStirring
  2. temperaturecooling
  3. temperatureis maintained for 30 minutes whereupon the mixture
  4. customto come to about 20° C.
  5. extractionthe solution is extracted three times with diethyl ether
  6. washThe ether extracts are washed
  7. dry with materialdried over sodium sulphate
  8. distillationthe ether is distilled off
  9. distillationDistillation of the residual oil

Sources & evidence

ORD record
ord-193db6b4b7bd411596c9c759271348d4
Source dataset
uspto-grants-1980_08
Patent number
US04218472

Reaction notes

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