Pivalaldehyde → Retinal

HRID 1534274Notes

Reaction equation

HRID 1534274 reaction equation
[CH3:1][C:2]([CH3:6])([CH3:5])[CH:3]=O.C[C:8]([CH3:13])([CH2:11][CH3:12])[CH:9]=O.[CH2:14]([C:16]([CH3:21])([CH2:19][CH3:20])C=O)[CH3:15].[CH3:22][C:23](C)([CH2:26][CH:27]=C)C=O.CC(C)(CCC)C=[O:33].CC(C)(C=C=C)C=O>>[CH3:22][C:23]1[CH2:26][CH2:27][CH2:3][C:2]([CH3:6])([CH3:5])[C:1]=1/[CH:12]=[CH:11]/[C:8](/[CH3:13])=[CH:9]/[CH:20]=[CH:19]/[C:16](/[CH3:21])=[CH:14]/[CH:15]=[O:33]

Participants

7

Reactant 6

HCID 12417Pivalaldehyde2×HCID 776782,2-Dimethyl-3,4-pentadienalHCID 796362,2-Dimethylpent-4-enal2×HCID 842922,2-DimethylvaleraldehydeHCID 137426Butanal, 2,2-dimethyl-HCID 15174357HCID 15174357, compound

Product 1

HCID 638015Retinal

Procedure

Examples of the aldehyde of the general formula (1) include trimethylacetaldehyde, 2,2-dimethylbutanal, 2-ethyl-2-methylbutanal, 2,2-dimethyl-4-pentenal, 2,2-dimethylpentanal, 2,2-dimethylpenta-3,4-dienal and the like. Particularly, trimethylacetaldehyde (boiling point 74° C. at 730 mmHg) and 2,2-dimethy-4-pentenal (boiling point 124° C. at 760 mmHg) are preferable examples of the invention because the both substances themselves and the corresponding alcohols formed at the preparation of vitamin A aldehyde as side products have lower boiling points, so that these materials can be easily removed from the reaction mixtures at lower temperatures after the completion of the reaction.

Sources & evidence

ORD record
ord-9dce8744d086419194eb3e2a210df7f1
Source dataset
uspto-grants-1992_02
Patent number
US05087762

Reaction notes

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