Water → HCID 54289147, compound

HRID 263135Notes

Reaction equation

HRID 263135 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[C@@H:6]([OH:9])[CH2:5][C:4]([CH3:11])([CH3:10])[C:3]=1[CH:12]=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=[O:17].N1C=CC=CC=1.[Cl:25][CH2:26][C:27](Cl)=[O:28].O>C(OCC)C>[CH3:1][C:2]1[C:7](=[O:8])[C@@H:6]([O:9][C:27](=[O:28])[CH2:26][Cl:25])[CH2:5][C:4]([CH3:10])([CH3:11])[C:3]=1[CH:12]=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 86736557HCID 86736557, compound

Product 1

HCID 54289147HCID 54289147, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

13 grams of 5-[2,6,6-trimethyl-oxo-4(S)-hydroxy-cyclohex-1-en-1-yl]-3-methyl-penta-2,4-dien-1-al (XIII) are dissolved in 200 ml of diethyl ether. 20 ml of pyridine are added to the solution at 0° C. and 12 g of chloroacetic acid chloride are then added dropwise. The mixture is stirred for 1 hour and then poured into water and extracted with diethyl ether. The 5-[2,6,6-trimethyl-3-oxo-4(S)-(chloroacetoxy)-cyclohex-1-en-1-yl]-3-methyl-penta-2,4-dien-1-al is isolated from the ether extract (IIA).

Workup

  1. extractionextracted with diethyl ether

Sources & evidence

ORD record
ord-e317e9c0d95545a0a6686b16e5e057ce
Source dataset
uspto-grants-1979_05
Patent number
US04156090

Reaction notes

Loading…