Table 1 Procedure and optimization of iodoform reaction of 1 with in situ-generated t-BuOIa.

From: One-step Conversion of Levulinic Acid to Succinic Acid Using I2/t-BuOK System: The Iodoform Reaction Revisited

Entry

1 in t-BuOH

H2O

Yield (%)c

(M)b

(eq.)

2

5

1

1.0

1.0

58

2

2

1.0

3.0

63

2

3

1.0

10

55

2

4d

1.0

3.0

69

2

5d

0.2

3.0

87(83)

2(2)

6d

2.2

3.0

64

2

7d,e

0.2

3.0

(67)

2

8d,f

0.2

3.0

8

4

9d

0.2

5.0

86

3

10d

0.2

1.0

85

2

  1. aReaction conditions: I2 (3 eq.), t-BuOK (9 eq.) in t-BuOH at rt for 5 min under argon. Initial net concentration of 1 in t-BuOH is 0.05 M.
  2. bConcentration of stock solution of 1 in t-BuOH.
  3. c1H NMR yields. Numbers in parentheses are isolated yields.
  4. d 1 in t-BuOH was added dropwise to a t-BuOI solution in t-BuOH over 10 min.
  5. e10 mmol scale.
  6. f t-BuONa was used instead of t-BuOK.
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