Sulfuric Acid → HCID 23346462, compound

HRID 1856281Notes

Reaction equation

HRID 1856281 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.CN(C)[CH:22]=[O:23].S(=O)(=O)(O)O>O1CCCC1.CCCCCC.C(OCC)C>[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:22]=[O:23])=[CH:3]2

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 6228DimethylformamideHCID 23346455HCID 23346455, compoundHCID 178418339Butyllithium

Product 1

HCID 23346462HCID 23346462, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To 3'-bromospiro(cyclopentane-1,1'-indene) (7.5 g) in tetrahydrofuran, (500 ml) is added at -70° C. a solution of n-butyllithium in hexane (200 ml of a 1.8 M solution) in two portions. The temperature is kept at -70° C. for a further 30 minutes. Dimethylformamide (73 g) is then added and the mixture is allowed to come to about 20° C. After 3 hours sulphuric acid (400 ml; 1 M) and diethyl ether (200 ml) are added. The ether phase is separated, washed with saturated sodium chloride solution and dried over sodium sulphate. Evaporation of the ether and distillation gives the title aldehyde; b.p. 130°-135° C./0.1 torr.

Workup

  1. customto come to about 20° C
  2. customThe ether phase is separated
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customEvaporation of the ether and distillation

Sources & evidence

ORD record
ord-4ddf022ba759440a8beb52ce9bd167b6
Source dataset
uspto-grants-1980_08
Patent number
US04218472

Reaction notes

Loading…