2,3,5-Triiodobenzoic acid → (3,5-Diiodophenyl)methanol

Reaction equation

I[C:2]1[C:10]([I:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4](O)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[I:11][C:10]1[CH:2]=[C:3]([CH:7]=[C:8]([I:12])[CH:9]=1)[CH2:4][OH:5]

Participants

Reactant 2

HCID 69482,3,5-Triiodobenzoic acid

HCID 21226445Aluminium lithium hydride

Product 1

HCID 12330868(3,5-Diiodophenyl)methanol

Procedure

Using the procedure of B, Gaux and D. LeHenaff, Bull. Soc. Chem. Fr., 34, 505 (1974), 2,3,5-triiodobenzoic acid (Aldrich) was treated with lithium aluminum hydride to give 3,5-diiodobenzyl alcohol with m.p. of 136.5°-140° (literature 137°). Using the procedure outlined in Example 4, 3,5-diiodobenzyl alcohol was treated with n-hexyl chloroformate giving s in Table I (ND25 =1.5800).

Sources & evidence

ORD record: ord-f4c91a5d5e8b43e7a55dc8f6e8b0d5ec
Source dataset: uspto-grants-1979_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04175544

Reaction notes

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