Sulfuric Acid → HCID 12878341, compound

HRID 224432Notes

Reaction equation

HRID 224432 reaction equation
[BH4-].[Na+].[O:3]=[C:4]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:12][C:11]=1[O:22][CH3:23])[CH2:5][CH2:6][C:7]([OH:9])=[O:8].OS(O)(=O)=O>O1CCOCC1.O>[OH:3][CH:4]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:12][C:11]=1[O:22][CH3:23])[CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 12878340HCID 12878340, compound

Product 1

HCID 12878341HCID 12878341, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent2×

Procedure

1.06 g of NaBH4 in 90 ml of dioxane-water (1:1) are added dropwise with stirring at room temperature to 1.16 g of 4-oxo-4-(4-cyclohexyl-2-methoxyphenyl)-butyric acid in 200 ml of dioxane-water (1:1). This is left to stand for 5 hours at 22° and then acidified with 2N H2SO4 to pH=2. Most of the dioxane is removed on rotary vapouriser and the aqueous solution is extracted three times with ethyl acetate. The organic phases are washed once with water, dried over Na2SO4 and concentrated. The residue is recrystallised twice from ether-petroleum-ether. M.p. 105°-106°.

Workup

  1. waitThis is left
  2. customMost of the dioxane is removed on rotary vapouriser
  3. extractionthe aqueous solution is extracted three times with ethyl acetate
  4. washThe organic phases are washed once with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue is recrystallised twice from ether-petroleum-ether

Sources & evidence

ORD record
ord-60ad8b2b3d9c485eb03e2b13583ce4f0
Source dataset
uspto-grants-1980_11
Patent number
US04232039

Reaction notes

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