Water → 7-{7-(3-Oxo-4-propoxybut-1-enyl)-1,4-dioxaspiro[4,4]-non-6-yl}heptanoic acid

HRID 259203Notes

Reaction equation

HRID 259203 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:17]([CH:18]=[CH:19][C:20](=[O:26])[CH2:21][O:22][CH2:23][CH2:24][CH3:25])[CH2:16][CH2:15][C:10]21[O:14][CH2:13][CH2:12][O:11]2.S(=O)(=O)(O)[OH:28].C(OCC)C.O>CN(C)C=O.[O-2].[O-2].[O-2].[Cr+6]>[O:26]=[C:20]([CH2:21][O:22][CH2:23][CH2:24][CH3:25])[CH:19]=[CH:18][CH:17]1[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH:9]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([OH:28])=[O:1]

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 572413446-(7-Hydroxyhepty)-7-(3-oxo-4-propoxybut-1-enyl)-1,4-dioxaspiro[4,4]nonane

Product 1

HCID 573107087-{7-(3-Oxo-4-propoxybut-1-enyl)-1,4-dioxaspiro[4,4]-non-6-yl}heptanoic acid

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6228DimethylformamideSolvent2×

Procedure

Chromium trioxide (9.8 g.) (dried over phosphorus pentoxide) was added portionwise with stirring to a solution of 6-(7-hydroxyhepty)-7-(3-oxo-4-propoxybut-1-enyl)-1,4-dioxaspiro[4,4]nonane (8.6 g.) in dry dimethylformamide (130 ml.) at a temperature lower than 0° C. Concentrated sulphuric acid (3.5 ml.) in dimethylformamide (130 ml.) was added and the mixture stirred at below 10° C. for 1 hour. Diethyl ether was added followed by a minimum quantity of water to produce two readily separable layers. The ether layer was separated and stirred with aqueous 2 N sodium carbonate solution. The aqueous layer was separated, washed with diethyl ether and then covered with a layer of diethyl ether and acidified to pH 5 by the addition of 20% aqueous sodium dihydrogen phosphate solution. The ethereal layer was separated and the aqueous layer again extracted with diethyl ether. The combined ethereal layers were dried over sodium sulphate and evaporated to give 7-{7-(3-oxo-4-propoxybut-1-enyl)-1,4-dioxaspiro[ 4,4]-non-6-yl}heptanoic acid (2.1 g.),

Workup

  1. customto produce two readily separable layers
  2. customThe ether layer was separated
  3. stirringstirred with aqueous 2 N sodium carbonate solution
  4. customThe aqueous layer was separated
  5. washwashed with diethyl ether
  6. additionacidified to pH 5 by the addition of 20% aqueous sodium dihydrogen phosphate solution
  7. customThe ethereal layer was separated
  8. extractionthe aqueous layer again extracted with diethyl ether
  9. dry with materialThe combined ethereal layers were dried over sodium sulphate
  10. customevaporated

Sources & evidence

ORD record
ord-cea396c9e8b142c197d1ec46493c1698
Source dataset
uspto-grants-1977_07
Patent number
US04036872

Reaction notes

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