Potassium Hydroxide → HCID 88845124, compound

HRID 1730090Notes

Reaction equation

[OH-].[K+].[CH2:3]([N:5]([CH2:8][CH2:9][CH2:10][CH2:11]/[C:12](/[CH3:27])=[CH:13]/[CH2:14][CH2:15]/[C:16](/[CH3:26])=[CH:17]/[CH2:18][CH:19](C(O)=O)[C:20]([OH:22])=[O:21])[CH2:6][CH3:7])[CH3:4]>>[CH2:3]([N:5]([CH2:8][CH2:9][CH2:10][CH2:11]/[C:12](/[CH3:27])=[CH:13]/[CH2:14][CH2:15]/[C:16](/[CH3:26])=[CH:17]/[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:6][CH3:7])[CH3:4]

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 88846084HCID 88846084, compound

Product 1

HCID 88845124HCID 88845124, compoundYield 34%

Procedure

450.5 g of geranylmalonic ester, 34.9 g of sodium and 227.3 g of diethylaminopropylchloride (b.p., 73°-78° C/20 mm) isolated from 423.3 g of hydrochloride, are heated in toluene to obtain 329.4 g of diethylaminopropylgeranylmalonic ester having a boiling point of 185°-210° C/2 mm, n20 1.4709. The 329.4 grams of diethylaminopropylgeranylmalonic ester are saponified with a concentrated solution of potassium hydroxide in alcohol to prepare 524.7 g of moist diethylaminopropylgeranylmalonic acid. The diethylaminopropylgeranylmalonic acid, either moist or dried, is then decarboxylated in vacuum (after dehydration of the acid in vacuum). 156 g of diethylaminopropylgeranylacetic acid are produced. The boiling point of the acid is 190°-200° C/2 mm, n20 1.4951.

Workup

dry with materialThe diethylaminopropylgeranylmalonic acid, either moist or dried

Sources & evidence

ORD record: ord-25ffd9624d1846089ae5bf5f98433350
Source dataset: uspto-grants-1976_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03991086

Reaction notes

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