Acetic Acid → Diisopropylether hexane

HRID 2072374Notes

Reaction equation

HRID 2072374 reaction equation
C=O.[C:3]1(S(O)=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:12]N(C)CCN(C)C.[C:20]([OH:23])(=O)[CH3:21]>C(Cl)(Cl)Cl>[CH:20]([O:23][CH:8]([CH3:7])[CH3:3])([CH3:21])[CH3:12].[CH3:7][CH2:8][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 12057Benzenesulfinic acid

Product 1

HCID 21881879Diisopropylether hexane

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1,18 g of 1β-tert.-butoxy-8aβ-methyl-1,2,3,4,6,7,8,8a-octahydronaphthalene-6-one, 0,175 g of paraformaldehyde, 0.90 g of benzenesulfinic acid, 2,4 ml of N,N,N',N'-tetramethylethylendiamine and 1,6 ml of glacial acetic acid is stirred for 2 days at 70° under nitrogen atmosphere. The reaction mixture is taken up in chloroform, washed with a saturated solution of sodiumhydrogencarbonate and with 1 n HCl. The organic phase is dried with sodium sulfate and the solvent removed under vacuum. The yield of 2,33 g of the crude product is purified on silica gel by means of chromatography (benzine/ethyl acetate 95:5 → 50:50). After recristallisation from diisopropylether/hexane 0.452 g of rac. 1β-tert.-butoxy-8aβ-methyl-5-(phenylsulfonylmethyl)-1,2,3,4,6,7,8,8a-octahydronaphthalene-6-one is thus obtained, m.p. 96° - 98°. ε252 = 12700.

Workup

  1. washwashed with a saturated solution of sodiumhydrogencarbonate and with 1 n HCl
  2. dry with materialThe organic phase is dried with sodium sulfate
  3. customthe solvent removed under vacuum
  4. customThe yield of 2,33 g of the crude product is purified on silica gel by means of chromatography (benzine/ethyl acetate 95:5 → 50:50)

Sources & evidence

ORD record
ord-fa931a1581c34f62bfd9dd08c80149b5
Source dataset
uspto-grants-1977_09
Patent number
US04051188

Reaction notes

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