Formic Acid → Camphor

HRID 1506724Notes

Reaction equation

C(O)(=O)CCC(C)=O.C(O)=O.O.[C:13]12([CH2:23]S(O)(=O)=O)[C:20]([CH3:22])([CH3:21])[CH:17]([CH2:18][CH2:19]1)[CH2:16][C:14]2=[O:15].C(O)CCCO>>[C:13]12([CH3:23])[C:20]([CH3:22])([CH3:21])[CH:17]([CH2:18][CH2:19]1)[CH2:16][C:14]2=[O:15]

Participants

Reactant 5

HCID 284Formic Acid

HCID 962Water

HCID 80641,4-Butanediol

HCID 11579Levulinic Acid2×

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-

Product 1

HCID 2537Camphor

Procedure

A crude levulinic acid composition comprising 14.9 g (0.128 mol) levulinic acid, 0.449 g (9.76×10−3 mol) formic acid, 30 g (1.66 mol) DI water, and 0.3484 g (1.50×10−3 mol) camphor sulfonic acid was esterified with 2.89 g (3.21×10−2 mol) 1,4-butanediol. The procedure for Example 6 was followed, and analysis of the reaction mixture by GC-FID showed a peak corresponding to LA-BDO-LA.

Sources & evidence

ORD record: ord-7b56b72675bf462baf70d16d8c0fd8e2
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221741B2

Reaction notes

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